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

HRID 5344

Reaction equation

HRID 5344 reaction equation
C[C:2]([CH3:5])([O-:4])C.[K+].[Br:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][C:9]=1[CH:16]([CH3:20])C([O-])=O.[C:21](OCC)(=[O:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23].O.C[CH2:33][O:34]CC>>[O:27]=[C:21]([CH:20]([C:33]([O:4][CH2:2][CH3:5])=[O:34])[CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[Br:7])[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 5

HCID 962WaterHCID 3283Diethyl Ether2×HCID 7268Diethyl OxalateHCID 23665647Potassium tert-butoxideHCID 1317181192-Bromo-5-methoxyphenyl-propionate

Product 1

HCID 156623402-Oxo-3-carboethoxy-4-(2-bromo-5-methoxyphenyl)butanoic acid, ethyl esterYield 90%

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 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) δ1.20 (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

  1. customthe aqueous layer was separated
  2. extractionextracted with ether
  3. dry with materialThe ether layer was dried (MgSO4)
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-29b1539b5e8e4303be8267bfa4999d0d
Source dataset
uspto-grants-1993_09
Patent number
US05244888

Linked notes

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