Water → 2-Oxo-3-carboethoxy-5-(2-bromo-5-methoxyphenyl)pentanoic acid ethyl ester

HRID 728575Notes

Reaction equation

HRID 728575 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][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].[C:24](OCC)(=[O:30])[C:25]([O:27][CH2:28][CH3:29])=[O:26].O>CCOCC>[CH2:28]([O:27][C:25](=[O:26])[C:24](=[O:30])[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:17][CH2:16][C:9]1[CH:10]=[C:11]([O:14][CH3:15])[CH:12]=[CH:13][C:8]=1[Br:7])[CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 7268Diethyl OxalateHCID 15662398Ethyl 4-(2-bromo-5-methoxy phenyl)butyrateHCID 23665647Potassium tert-butoxide

Product 1

HCID 156623992-Oxo-3-carboethoxy-5-(2-bromo-5-methoxyphenyl)pentanoic acid ethyl esterYield 89%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

Potassium t-butoxide (26.94 g) was suspended in 130 ml of anhydrous ether and cooled to 0° C. A solution of 60.24 g ethyl 4-(2-bromo-5-methoxy phenyl)butyrate and 43.84 g diethyl oxalate in 60 ml ether was added dropwise over 20 min. After 2 h at 25° C., the reaction was poured into 400 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 71.26 g of the desired product as a colorless oil (89%). NMR (CDCl3) δ 1.25 (t, 3H), 1.4 (t, 3H), 2.25 (m, 2H), 2.75 (m, 2H), 3.78 (s, 3H), 4.0-4.5 (m, 5H), 6.64 (dd, 1H), 6.79 (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-054d18abf5d7411184712916b0e07e7b
Source dataset
uspto-grants-1991_09
Patent number
US05049564

Reaction notes

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