Triethyl Citrate → Diethyl Citrate

HRID 743718

反応式

HRID 743718 の反応式
[C:1]([O:17][CH2:18][CH3:19])(=[O:16])[CH2:2][C:3]([CH2:10][C:11]([O:13]CC)=[O:12])([C:5]([O:7][CH2:8][CH3:9])=[O:6])[OH:4].[OH-].[Na+]>C(O)C.O>[OH:4][C:3]([C:5]([O:7][CH2:8][CH3:9])=[O:6])([CH2:2][C:1]([O:17][CH2:18][CH3:19])=[O:16])[CH2:10][C:11]([OH:13])=[O:12]

参加物

5

反応物 2

HCID 6506Triethyl CitrateHCID 14798Sodium Hydroxide

生成物 1

HCID 15384083Diethyl Citrate収率 28.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

A solution of triethyl citrate (34.1 g, 123 mmol) in ethanol and water (30 ml) is treated with sodium hydroxide (3.70 g, 92.6 mmol) and stirred at room temperature under argon for 4.5 hours. The reaction mixture is concentrated on a rotary evaporator then diluted with water (50 ml). The pH is adjusted to ca. 1 using 2N HCl. The aqueous solution is then extracted with a large excess of chloroform (4×150 ml). The combined organic layers are dried (MgSO4), filtered and concentrated to give crude oil. Purification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2) gives 8.72 g of product (38% as a racemate.

後処理

  1. concentrationThe reaction mixture is concentrated on a rotary evaporator
  2. additionthen diluted with water (50 ml)
  3. extractionThe aqueous solution is then extracted with a large excess of chloroform (4×150 ml)
  4. dry with materialThe combined organic layers are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give crude oil
  8. customPurification by flash chromatography (5% MeOH/CH2Cl2 to 1% AcOH/5%MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-411ed25710a04d778d1ae23090065934
出典データセット
uspto-grants-1996_09
特許番号
US05556990

関連ノート

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