Fluka

To seat ch for available starting materials, similarity searches, substructure searches, and some classical retrieval methods such as full structure searches, name searches, empirical formula searches, etc., have been integrated into the system. All searches can be applied to a number of catalogs of available fine chemicals (c.g, Fluka 154]. In addition, compound libraries such as in-housc catalogs can easily be integrated. 

Both precursor compounds, 3 and 4, arc available from Fluka, which is checked automatically Iry WODCA searching in this data file. 

Pyridyl)hydrazine (Aldrich), 4-acetylpyridine (Acros), N,N,N -trimethylethylenediamine (Aldrich), methylrhenium trioxide (Aldrich), InQj (Aldrich), Cu(N0j)2-3H20 (Merck), Ni(N03)2-6Il20 (Merck), Yb(OTf)3(Fluka), Sc(OTf)3 (Fluka), 2-(aminomethyl)pyridine (Acros), benzylideneacetone (Aldrich), and chalcone (Aldrich) were of the highest purity available. Borane dimethyl sulfide (2M solution in THE) was obtained from Aldrich. Methyl vinyl ketone was distilled prior to use. Cyclopentadiene was prepared from its dimer immediately before use. (R)-l-acetyl-5-isopropoxy-3-pyrrolin-2-one (4.15) has been kindly provided by Prof H. Hiemstra (University of Amsterdam). 

W. E. Keller, Phase TransferReactions—Fluka-Compedium, Vol. 1, G. Thieme Vedag, Stuttgart, New York, 1986 Vol. 2, 1987. 

This complex should be used when the organolithium is in solution in a hydrocarbon solvent. For organolithium reagents prepared in ether (see Note 4), the same complex may be used or, more conveniently, copper iodide (Cull can be used. The Cul purchased from Prolabo or Merck 4 Company, Inc. may be used directly. Other commercial sources of Cul (Fluka, Aldrich Chemical Company, Inc., Alfa Products, Morton/Thiokol, Inc.) furnish a salt which affords better results when purified. 1 mol of Cul is stirred for 12 hr with 500 ml of anhydrous tetrahydrofuran, then filtered on a sintered glass funnel ( 3), washed twice with 50 ml of anhydrous tetrahydrofuran, once with 50 ml of anhydrous ether and finally dried under reduced pressure (0.1 imO for 4 hr. 

The ethyl 2-oxocyclohexanecarboxylate used was Fluka AG practical grade, and was distilled (bp 106-108 C/12 mm) before use. 

N,N-D1methylformam1de from Carlo Erba Chemicals, from Fluka AG, or from Merck 4 Company, Inc. was used as received. Other solvents (for example, acetone, acetic acid, acetonitrile) can also be used. 

The starting allyltrimethylsilane can be prepared in satisfactory yield by the procedure of Sommer. It can also be purchased from PCR Inc., Aldrich Chemical Company, Inc., Fluka A. G., Petrarch Systems Inc., and Tokyo Kasei Kogyo Co., Ltd. The checkers employed material from Petrarch. 

The product 1s somewhat hygroscopic and should Be stored 1n an airtight container. It Is also available as Lawesson s reagent from Aldrich, Fluka, and from Merck-Schuchard. 

The catalyst, 3-benzyl-5-(2-hydroxyethyl )-4-methyl-l, 3-thiazoHum chloride, is supplied by Fluka AG, Buchs, Switzerland, and by Tridom Chemical, Inc., Hauppauge, New York. The thiazolium salt may also be prepared as described below by benzylation of 5-(2-hydroxyethyl)-4-methyl-l,3-thiazole which is commercially available from E. Merck, Darmstadt, West Germany, and Columbia Organic Chemicals Co., Inc., Columbia, SC. The acetonitrile used by the checkers was dried over Linde 3A molecular sieves and distilled under nitrogen, bp 77-78°C. The same yield of thiazolium salt was obtained by the checkers when benzyl chloride and acetonitrile from commercial sources were used without purification. 

Triethylamine was supplied by Fluka A6 and Aldrich Chemical Company,... 

Propionyl chloride was purchased from Fluka AG and Aldrich Chemical Company, Inc. and was freshly distilled at 78-80°C (760 mm) prior to use. 

An extensive list of the commercially available resins is available from Sigma-Aldrich (www.sigmaaldrich.com), Novabiochem (www.novabiochem.com), Fluka and other chemical companies. Sigma-Aldrich and Novabiochem have excellent catalogs. In addition, the Novabiochem catalog and website are a rich source of useful technical information. 

The submitters used rhodium(III) oxide available from Fluka A G without further purification. The checkers obtained rhodium(III) oxide from Alfa Inorganics. 

The cyclohexene was purified by distillation over sodium metal before use (n D 1.4452). The submitters used the product available from Fluka A G, and the checkers used the product available from Aldrich Chemical Company, Inc. 

The submitters used product available from Fluka A G that was dried under reduced pressure after recrystallization from heptane at — 70°. 

The submitters used sodium amide (obtained from Fluka A G as small lumps under kerosene) which was washed with anhydrous tetra-hydrofuran and ground with a mill. The checkers used freshly opened and recently purchased cans of sodium amide powder (Fisher Scientific Company) older reagent gave unsatisfactory results. 

Chloro-2-methylpropene (methallyl chloride) is available from Fluka A G and Eastman Organic Chemicals. The chloride, b.p. 72° (760 mm.), was distilled before use. 

Catalyst obtained from Engelhard Industries was used. The submitters used 200 mg. of Fluka 10% palladium on charcoal catalyst with 5 g. of starting material in 250 ml. of ethanol and obtained a total yield of 2.3 g. (46%), m.p. 208-211°. 

Commercially available anhydrous sodium p-toluenesulfinate, purum, ca. 97% (Fluka A G, Busch S.G., Switzerland) was used. 

The submitters used iron pentacarbonyl pract. grade obtained from Fluka A G. The checkers used iron pentacarbonyl obtained from Merok, Germany. 

Visit http //cortex.uchc.edu/ safety/ehs/msds-l.html. This site is accessible by UCHC network registered users only. Once registered, you can access 70,000 MSDSs from Sigma, Aldrich, and Fluka on-line. The MSDSs are available in several languages (English, French, German, Spanish and Italian languages). Updates are done on a quarterly basis. 

For a review on silylating agents, see G. van Look, G. Simchen. and J. Heberle, Silylating Agents Fluka Chemie AG, 1995. 

Besides Solvent Innovation, a number of other commercial suppliers nowadays offer ionic liquids in larger quantities [7]. Moreover, the distribution of these liquids by Fluka [8], Acros Organics [9], and Wako [10] assures a certain availability of different ionic liquids on a rapid-delivery basis. 

A list of current commercial suppliers of tetrafluoroborate and hexafluo-rophosphate salts includes (with no guarantee of completeness) Solvent Innovation GmbH, Kdln (www.sol-vent-innovation.com). Sachem Inc. (www.sacheminc.com), Fluka (www.fluka.com), Acros Organics (WWW. acros.be), and Wako (www.wako-chem.co. j p). 

R)- and (S)-2-I Iydroxy-1.2,2-triphenylcthyl acetate are commercially available from Merck, Darmstadt, Germany and from Newport Pharmaceuticals, Ireland. The (R)-enantiomer is also available from Fluka and Chiron. 

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