Ethyl phenylacetate → HCID 21188797, compound

Participants

Reaction Conditions

Reaction Steps

Diisopropylamine (2.71 ml, 1.1 eq) was added to dry THF (10 ml) and cooled to -78° C. N-butyllithium (11.01 ml of 1.6 Molar, 1.1 eq) was added dropwise. The mixture was stirred at -78° C. for 30 minutes and ethyl-2-phenylacetate (2.9 g, 1.0 eq) was dissolved in dry THF (20 ml) and the solution added dropwise to the reaction mixture. The mixture was stirred at -78° C. for 0.25 hour and then allowed to warm to -30° C. and stirred for an additional 0.25 hour. 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU) (2.13 ml, 1.0 eq) was dissolved in dry THF (20 ml) and added dropwise to the mixture. The resulting mixture was maintained at -30° C. for ten minutes. This mixture was then cannulated under N2 pressure to a flask which had been charged with ethyl ether (100 ml) and 1-bromo-2-chloroethane (7.3 ml, 5.0 eq) at -10° C. The mixture was stirred for three hours at -10° C. to -5° C. The mixture was cooled to -30° C. and quenched with a saturated ammonium chloride solution. The mixture was extracted with ethyl ether which was then dried over K2CO3. The solvent was stripped to provide 3.2 g of product which distilled at 70°-71° C. under 0.01 mmHg.

Provenance & Evidence