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

HRID 1090326노트

반응식

HRID 1090326 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f7f7f5c7be3f412ebde8b808fdf00c0f
출처 데이터셋
uspto-grants-1992_01
특허 번호
US05081238

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