Water → 2-Oxo-3-carboethoxy-4-(2-bromo-5-methoxyphenyl)butanoic acid, ethyl ester

HRID 728568Notes

Reaction equation

CC(C)([O-])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19].[C:23](OCC)(=[O:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CCOCC>[O:29]=[C:23]([CH:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[Br:7])[C:24]([O:26][CH2:27][CH3:28])=[O:25]

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium t-butoxide (6.72 g) was suspended in 30 ml of anhydrous ether and cooled to 0° C. A solution of 14.35 g of ethyl 3-(2-bromo-5-methoxyphenyl)propionate and 10.95 g diethyl oxalate in 10 ml ether was added dropwise over 15 min. After 2 h at 25° C., the reaction was poured into 100 ml H2O and the aqueous layer was separated, acidified to pH 1 and extracted with ether. The ether layer was dried (MgSO4) and the solvent was evaporated to yield 17.48 g of the desired product as a colorless oil (90%). NMR (CDCl3) δ 1.20 (t, 3H), 1.35 (t, 3H), 3.32 (dd, 2H), 3.76 (s, 3H), 4.18 (q, 2H), 4.32 (q, 2H), 4.53 (t, 1H), 6.67 (dd, 1H), 6.80 (d, 1H), 7.40 (d, 1H).

Workup

customthe aqueous layer was separated
extractionextracted with ether
dry with materialThe ether layer was dried (MgSO4)
customthe solvent was evaporated

Sources & evidence

ORD record: ord-a2c3dd98283041a0a80f9f2e2dba5a7d
Source dataset: uspto-grants-1991_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05049564

Reaction notes

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