Imidazole → 3-(tert-Butyldimethylsiloxy)butyric acid methyl ester

HRID 1090326ノート

反応式

HRID 1090326 の反応式
[OH:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C=O)C>[Si:14]([O:1][CH:2]([CH3:8])[CH2:3][C:4]([O:6][CH3:7])=[O:5])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

参加物

5

反応物 3

HCID 795ImidazoleHCID 15146Methyl 3-hydroxybutyrateHCID 28928tert-Butyldimethylsilyl chloride

生成物 1

HCID 137127793-(tert-Butyldimethylsiloxy)butyric acid methyl ester収率 91%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

5.91 Grams (50 mmol) of methyl 3-hydroxybutyrate and 3.74 g (55 mmol) of imidazole were dissolved in 20 ml of DMF and thereto 8.29 g (55 mmol) of t-butyldimethylsilylchloride was added in several portions. After stirring the mixture at room temperature for 30 minutes, ice water was added and extraction with diethyl ether was conducted three times. The extract was washed with a saturated solution of NaCl, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The concentrate was distilled (62° to 68° C./5 mmHg) to give 10.51 g of methyl (-)-3-t-butyldimethylsilyloxybutyrate (yield: 91%).

後処理

  1. extractionextraction with diethyl ether
  2. washThe extract was washed with a saturated solution of NaCl
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. distillationThe concentrate was distilled (62° to 68° C./5 mmHg)

出典と根拠

ORDレコード
ord-f7f7f5c7be3f412ebde8b808fdf00c0f
出典データセット
uspto-grants-1992_01
特許番号
US05081238

反応ノート

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