Diethyl Oxalate → Ethyl 2-(5-acetylamino-2-methylphenyl)-2-oxoacetate

HRID 29820Notes

Reaction equation

[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7](Br)[CH:6]=1)(=[O:3])[CH3:2].[Li]CCCC.CCCCC.[C:23](OCC)(=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25]>C1COCC1>[C:1]([NH:4][C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([C:23](=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:6]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of N-acetyl-3-bromo-4-methylaniline (1.43 g, 627 mmol) in THF (50 mL) at −78° C. is added 2M BuLi in pentane (7.83 mL, 15.66 mmol) dropwise. After a further 1 h, diethyl oxalate (4.26 mL, 31.3 mmol) is added. After stirring for 4 hours at −78° C., the reaction mixture is quenched with saturated NH4Cl solution. The mixture is partitioned between ethyl acetate and water. The layer is separated and the aqueous layer is extracted with ethyl acetate. The combined organic extracts are washed with brine, dried over Na2SO4, filtered and concentrated. The residue is purified by column chromatography (silica gel, eluting with ethyl acetate; hexanes from 1/1 to 2/1) to afford fee title compound (0.82 g, 52%).

Workup

customthe reaction mixture is quenched with saturated NH4Cl solution
customThe mixture is partitioned between ethyl acetate and water
customThe layer is separated
extractionthe aqueous layer is extracted with ethyl acetate
washThe combined organic extracts are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue is purified by column chromatography (silica gel, eluting with ethyl acetate; hexanes from 1/1 to 2/1)

Sources & evidence

ORD record: ord-c58acdacc1d440f98157c8b743cfb86d
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07423038B2

Reaction notes

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