2- ethoxymethyl

Thiazole acid chlorides react with diazomethane to give the diazoketone. The later reacts with alcoholic hydrogen chloride to give chloroacetylthiazole (Scheme 16). However, the Wolff rearrangement of the diazoketone is not consistently satisfactory (82). Heated with alcohol in the presence of copper oxide the 5-diazomethylketone (24) gives ethyl 5-thiazoleacetate (25) instead of the expected ethoxymethyl 5-thiazolyl ketone (Scheme 17) (83). 

SolubiHty parameters of 19.3, 16.2, and 16.2 (f /cm ) (7.9 (cal/cm ) ) have been determined for polyoxetane, po1y(3,3-dimethyl oxetane), and poly(3,3-diethyloxetane), respectively, by measuring solution viscosities (302). Heat capacities have been determined for POX and compared to those of other polyethers and polyethylene (303,304). The thermal decomposition behavior of poly[3,3-bis(ethoxymethyl)oxetane] has been examined (305). 

Properties have been determined for a series of block copolymers based on poly[3,3-bis(ethoxymethyl)oxetane] and poly [3,3-bis(methoxymethyl)oxetane]- (9-tetrahydrofuran. The block copolymers had properties suggestive of a thermoplastic elastomer (308). POX was a good main chain for a weU-developed smectic Hquid crystalline state when cyano- or fluorine-substituted biphenyls were used as mesogenic groups attached through a four-methylene spacer (309,310). Other side-chain Hquid crystalline polyoxetanes were observed with a spacer-separated azo moiety (311) and with laterally attached mesogenic groups (312). 

Trimethylpyrazole (336) adds dichlorocarbene generated under basic conditions (CHCla-EtONa) to give 10% of 4-dichloromethyl-3,4,5-trimethylisopyrazole (337 Scheme 28) (bromine also transforms (336) into an isopyrazole (312) Section 4.04.2.1.4(v)). Treatment with sodium ethoxide results in ring expansion of (337) into an ethoxymethyl-pyridazine (338) (B-76MI40402). 

Imidazole, l-ethoxymethyl-2,4,5-tribromo-lithiation, S, 416 Imidazole, 2-ethyl-chlorination, S, 398 Imidazole, 4-ethyl-synthesis, S, 484 Imidazole, N-ethyl-synthesis, S, 108... 

Trimethylsilyl)ethoxymethyl Ether (SEMOR) Me3SiCH2CH20CH20R Formation... 

Trimethylsilyl)ethoxymethyl chloride (SEMCl) [76513-69-4] M 166.7, b 57-59"/8mm, d 0.942, n 1.4350. Dissolve in pentane, dry (MgS04), evaporate and dist residual oil in a vac. Stabilise with lOppm of diisopropylamine. Store under N2in a sealed container in a refrigerator. [Lipshutz and Pegram Tetrahedron Lett 21 3343 I980. ... 

AIH2CI, AIHCI2, or BH3 in toluene or THE. See the section on SEM ethers for a selectivity study of these reagents with the SEM, MTM, EOM (ethoxymethyl), andp-AOM groups."... 

Methoxymethyl. 257 Benzyloxymethyl, 258 Methoxyethoxymethyl, 258 2-(Trimethylsilyl)ethoxymethyl, 259 Methylthiomethyl, 259 Phenylthiomethyl, 259 Azidomethyl, 260 Cyanomethyl, 260 2,2-Dichloro-1,1-difluoroethyl, 260 2-Chloroethyl, 261 2-Bromoethyl, 261 Tetrahydropyranyl, 261 1-Ethoxyethyl, 261 Phenacyl, 262... 

Fluorenylmethyl, 387 Methoxymethyl, 388 Methylthiomethyl, 389 Tetrahydropyranyl, 390 Tetrahydrofuranyl, 390 Methoxyethoxymethyl, 390 2-(Trimethylsilyl)ethoxymethyl, 391 Benzyloxymethyl, 391 Pivaloyloxymethyl, 391 Phenylacetoxymethyl, 392 Triisopropylsilylmethyl, 392 Cyanomethyl, 392 Acetol, 393 Phenacyl, 393... 

Removal of the the related ethoxymethyl group from an imidazole with 6 N HCl at reflux is slow and low yielding. Small structural effects at a site seemingly remote from the MOM group can have a significant influence on the deprotection process. The MOM group in compound a is easily removed with acid, but the cleavage with HCl in compound b proved quite difficult. ... 

Ethyl 9-ethoxycarbonyl- and 9-hydroxymethyl-3-methyl-6-oxo-2/f,6//-pyrido[2,l-Z>][l,3]thiazine-4-carboxylates were isomerized into 4H,6H-pyrido[2,l-b][l,3]thiazine-4-carboxylates by treatment with KOH overnight at room temperature and by treatment with NaOEt at 0 °C for 1 h and room temperature for 3h in EtOH, respectively. In another experiment, when the 9-hydroxymethyl derivative was treated with NaOEt in EtOH at — 10°C for 3h, a 2.5 1 mixture of ethyl 3,4-cw-H-9-ethoxymethyl-3-methyl-6-oxo-3,4-dihydro-2//,6//-pyrido[2,l-Z)][l,3]thiazine-4-carboxylate and the aforementioned 4//,6//-isomer were obtained (00JCS(P1)4373). 

The starting material is prepared by reacting 2-amino-6-methylpyridine with ethoxymethyl-ene-malonic acid diethyl ester and then reacting that product with sodium hydroxide. 

Chemical Name 2-((2,6-Dichloro-3-methylphenyl)emino] benzoic acid ethoxymethyl ester Common Name Etoclofene Structural Formula ... 

Ethoxymethyl)phthalonitriie (12 2,88 g, 15.5 mmol), Fe(OAc)2 (672 mg, 3.9 mmol), and two drops of DBU were heated in anhyd hexan-l-ol (120 mL) at 150rC until all the phthalonitrile had reacted (TLC). The mixture was cooled and the solvent was removed under reduced pressure. The residue was washed with McOH and purified by column chromatography [neutral alumina (deactivated with 4% H,0), CHC1, ... 

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