Acetic acid, 2-phenoxy-, ethyl ester → HCID 15080405, compound

HRID 477576

Reaction equation

C([Li])CCC.[CH3:6][S:7]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(=[O:9])=[O:8].[O:16]([CH2:23][C:24](OCC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O1CCCC1>[C:10]1([S:7]([CH2:6][C:24](=[O:25])[CH2:23][O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:9])=[O:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

Conditions

Temperature: -20 °C

Procedure

n-Butyllithium (8.5 ml, 1.6M in hexane) was added at -72° C. to a solution of methylphenyl sulfone (2.14 g, 13.7 mmol) in 80 ml of tetrahydrofuran. The reaction mixture was then allowed to warm slowly to -20° C. and maintained at this temperature for 25 minutes. It was then recooled to -72° C. and ethyl phenoxyacetate (1.48 g, 8.22 mmol) was added dropwise. The cooling bath was removed, the mixture was stirred at 20° C. for 14 hrs. and then poured into 100 ml of saturated NH4Cl and extracted with diethyl ether. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulfate and the solvent removed under reduced pressure. The crude residue was purified by column chromatography (silica gel, methylene chloride) giving 1-phenylsulfonyl-2-oxo-3-phenoxypropane, the compound of formula (2a), 800 mg.

Workup

temperaturemaintained at this temperature for 25 minutes
customwas then recooled to -72° C.
customThe cooling bath was removed
additionand then poured into 100 ml of saturated NH4Cl
extractionextracted with diethyl ether
washThe combined organic extracts were washed with brine
dry with materialdried over anhydrous magnesium sulfate
customthe solvent removed under reduced pressure
customThe crude residue was purified by column chromatography (silica gel, methylene chloride)

Sources & evidence

ORD record: ord-2cd40da7323a4651b90ebe714304744b
Source dataset: uspto-grants-1989_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04888358

Linked notes

Loading…