Imidazole → HCID 178501292、化合物

HRID 1503970ノート

反応式

HRID 1503970 の反応式
[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]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178501285HCID 178501285、化合物

生成物 1

HCID 178501292HCID 178501292、化合物収率 96%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-403beb529f484230a39527c1976b3eca
出典データセット
uspto-grants-2015_12
特許番号
US09212190B2

反応ノート

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