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

HRID 5344

反応式

HRID 5344 の反応式
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]

参加物

6

反応物 5

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

生成物 1

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

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-29b1539b5e8e4303be8267bfa4999d0d
出典データセット
uspto-grants-1993_09
特許番号
US05244888

関連ノート

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