Ethyl chloromethyl ether

To a solution of 0.40 mol of butyllithium in about 280 ml of hexane were added 280 ml of dry THF with cooling below -10°C. Subsequently 0.40 mol of 1,1-diethoxy--2-propyne (see Chapter V, Exp. 28) was introduced in 15 min at -30 to -10°C. To the solution obtained was then added in 15 min with cooling at about -15°C 0.40 mol of chloromethyl ethyl ether (note 2). After the addition stirring was continued for 1 h without cooling. The mixture was then shaken with concentrated ammonium chloride solution and the ethereal layer was separated off. The aqueous layer was extracted twice with diethyl ether. After drying the ethereal solutions over magnesium sulfate the diethyl ether was evaporated in a water-pump vacuum. 

N-2,6-Dichloro-m-tolylanthranilic acid Chloromethyl ethyl ether... 

Chloro-2-methyl-3-d i met hylamino-propane T rimeprazine Chloromethyl ethyl ether Terofenamate... 

Carbon tetrachloride, 0322 Carbon tetrafluoride, 0349 Carbon tetraiodide, 0525 f 1-Chlorobutane, 1637 f 2-Chlorobutane, 1638 f Chlorocyclopentane, 1923 f l-Chloro-l,l-dilluoroethane, 0731 Chlorodilluoromethane, 0369 f Chloroethane, 0848 Chloroform, 0372 f Chloromethane, 0432 f l-Chloro-3-methylbutane, 1986 f 2-Chloro-2-methylbutane, 1987 f Chloromethyl ethyl ether, 1246 f Chloromethyl methyl ether, 0850 f l-Chloro-2-methylpropane, 1639 f 2-Chloro-2-methylpropane, 1640 f 1-Chloropentane, 1988 f 1-Chloropropane, 1243 f 2-Chloropropane, 1244 f l-Chloro-3,3,3-trifluoropropane, 1127 1,2-Dibromoethane, 0785 Dibromomethane, 0395... 

Chloromethyl ethyl ether 98 was lithiated in the presence of a catalytic amount of DTBB (5%) and an electrophile in THF at 0°C, to give after hydrolysis the expected functionahzed ethers 99 (Scheme 41) . Alternatively, the same process can be carried out in a two-step reaction, but performing the lithiation at —90°C in order to avoid the decomposition of a-ethoxymethyllithium 100 followed by the introduction of the electrophile. 

Dichlorodimethyltitanium, 216 Intramolecular alkylation 9-Bromo-9-phenylfluorene, 48 Chloromethyl ethyl ether, 75 Di-p-carbonylhexacarbonyldicobalt, 99 l-Hydroxy-3-trimethylsilylmethyl-3-butene, 147 Menthol, 172 Potassium t-butoxide, 252 Miscellaneous alkylations at active hydrogens... 

Dimethylthexylsilyl trifluorometh-anesulfonate, 74 using other methods Allyl chloroformate, 9 Benzyl trichloroacetimidate, 32 Bromodimethylborane, 47 Chloromethyl ethyl ether, 75 2,3-Dihydro-1,4-dioxin, 112 p-Methoxyphenol, 181 of aldehydes and ketones as acetals or dithioacetals... 

Boron trifluoride etherate, 43 Chloromethyl ethyl ether, 75 Lithium 4,4 -di-t-butylbiphenylide, 162... 

Norephedrine, 200 Organoaluminum reagents, 202 Organotitanium reagents, 213 9-(Phenylseleno)-9-borabicyclo-[3.3.1]nonane, 245 Tin(II) chloride, 298 Titanium(IV) chloride, 304 Trityllithium, 338 Trityl perchlorate, 339 Zinc chloride, 349 By other reactions Chloromethyl ethyl ether, 75 Dibutyltin oxide, 95 Samarium(II) iodide, 270 Tributyltin hydride, 316 Hydroxy amides a-Hydroxy amides... 

CHLOROMETHYL)ETHYLENE OXIDE see EAZ500 CHLOROMETHYL ETHYL ETHER see CIMOOO (2-CHLORO-l-METHYLETHYL) ETHER see BII250... 

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