Water → Ethyl 2-hydroxycyclopentanecarboxylate

HRID 2214059ノート

反応式

HRID 2214059 の反応式
[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=[O:11])=[O:5])[CH3:2].[BH4-].[Na+].O>C(O)C>[CH2:1]([O:3][C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][CH:7]1[OH:11])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 962WaterHCID 69136Ethyl 2-oxocyclopentanecarboxylateHCID 4311764Sodium borohydride

生成物 1

HCID 275611Ethyl 2-hydroxycyclopentanecarboxylate収率 84%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
0 °C

実験手順

A solution of 2-oxo-cyclopentanecarboxylic acid ethyl ester (10 g, 64.0 mmol) in ethanol (106.7 mL) cooled to 0° C. was treated with 98% sodium borohydride (686 mg, 17.78 mmol). The reaction was stirred at 0° C. for 30 min. At this time, the reaction mixture was poured into water (53 mL) and was extracted into diethyl ether (3×100 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230–400 mesh, 75/25 ethyl acetate/hexanes) afforded 2-hydroxy-cyclopentanecarboxylic acid ethyl ester (8.5 g, 83.9%) as a clear liquid.

後処理

  1. extractionwas extracted into diethyl ether (3×100 mL)
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-f468ddf4ab0b415abdb51b41a538aafa
出典データセット
uspto-grants-2006_09
特許番号
US07105671B2

反応ノート

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