Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl ester → Ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate

HRID 133792

反応式

HRID 133792 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:16])[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:5][CH:4]=1.[BH4-].[Na+]>CO.S([O-])([O-])(=O)=O.[Na+].[Na+]>[OH:16][CH:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)[CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12]

参加物

5

反応物 2

HCID 76150Benzenepropanoic acid, 4-methoxy-beta-oxo-, ethyl esterHCID 4311764Sodium borohydride

生成物 1

HCID 11096232Ethyl 3-hydroxy-3-(4-methoxyphenyl)propanoate収率 56.2%

試薬・触媒・溶媒 2

HCID 24436Sodium Sulfate触媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of ethyl 3-(4-methoxyphenyl)-3-oxopropanoate (444 mg, 2 mmol) in methanol (4 mL) was added sodium borohydride (76 mg, 2.0 mmol) at 0° C. slowly. After addition, the reaction mixture was stirred at 0° C. for 30 min. Two drops of saturated sodium sulfate solution were added to the reaction mixture to quench the reaction. Methanol was removed in vacuo, and water was added to the residue. The aqueous solution was extrated with ethyl acetate (x3), and the combined organic layers were dried over anhydrous sodium sulfate, and filtered. The filtrate was evaporated in vacuo. The crude mixture was purified by Flash Chromatography with eluent of 40% ethyl acetate/60% hexane to give the title compound as a clear oil (252 mg, 56% yield). 1H NMR (400 MHz, CDCl3) δ 1.22-1.28 (m, 3 H) 2.63-2.75 (m, 2 H) 3.79 (s, 3 H) 4.16 (q, J=7.13 Hz, 2 H) 5.07 (dd, J=9.06, 3.78 Hz, 1 H) 6.85-6.89 (m, 2 H) 7.24-7.31 (m, 2 H). HPLC retention time: 1.973 min (method A). MS (ESI) (M+Na)+ 246.96.

後処理

  1. additionAfter addition
  2. customto quench
  3. customthe reaction
  4. customMethanol was removed in vacuo, and water
  5. additionwas added to the residue
  6. dry with materialthe combined organic layers were dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated in vacuo
  9. customThe crude mixture was purified by Flash Chromatography with eluent of 40% ethyl acetate/60% hexane

出典と根拠

ORDレコード
ord-8116151a36d54ab390cb89a4201515d4
出典データセット
uspto-grants-2008_06
特許番号
US07390925B2

関連ノート

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