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

HRID 5344

반응식

HRID 5344 반응식
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]

참가 물질

6

반응물 5

HCID 962WaterHCID 3283Diethyl Ether2회HCID 7268Diethyl OxalateHCID 23665647Potassium tert-butoxideHCID 1317181192-Bromo-5-methoxyphenyl-propionate

생성물 1

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

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-29b1539b5e8e4303be8267bfa4999d0d
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244888

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