Imidazole → HCID 178501292, 화합물

HRID 1503970노트

반응식

HRID 1503970 반응식
[OH:1][C@H:2]1[CH2:7][CH2:6][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.N1C=CN=C1.[C:17]([Si:21](Cl)([CH3:23])[CH3:22])([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C>[Si:21]([O:1][C@H:2]1[CH2:3][CH2:4][C@H:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178501285HCID 178501285, 화합물

생성물 1

HCID 178501292HCID 178501292, 화합물수율 96%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A 500-mL round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was charged with a solution of methyl trans-4-hydroxycyclohexane-1-carboxylate (16.6 g, 104.93 mmol, 1.00 equiv) and imidazole (14.28 g, 180.53 mmol, 1.72 equiv) in distilled DMF (25 mL). Tert-butyl(chloro)dimethylsilane (28.3 g, 187.76 mmol, 1.79 equiv) was added slowly and the resulting solution was stirred for 14 hrs at room temperature. After completion, the reaction was then quenched with water and extracted with 3×200 mL of ethyl acetate. The combined organic layers were washed with water, brine and dried over sodium sulfate. After concentration under reduced pressure, the residue was applied onto a silica gel column with ethyl acetate/petroleum ether (10:1) to give the desired methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexane-1-carboxylate (27.4 g, 96%) as a colorless oil.

후처리

  1. customA 500-mL round-bottom flask, purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. customAfter completion, the reaction was then quenched with water
  4. extractionextracted with 3×200 mL of ethyl acetate
  5. washThe combined organic layers were washed with water, brine
  6. dry with materialdried over sodium sulfate
  7. concentrationAfter concentration under reduced pressure

출처 및 근거

ORD 기록
ord-403beb529f484230a39527c1976b3eca
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212190B2

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