Imidazole → Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

HRID 56827노트

반응식

HRID 56827 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:3]1.[Si:12](Cl)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13].N1C=CN=C1>CN(C)C=O>[Si:12]([O:1][CH:2]1[CH2:3][CH2:4][CH:5]([C:8]([O:10][CH3:11])=[O:9])[CH2:6][CH2:7]1)([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

참가 물질

5

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 87117Methyl 4-hydroxycyclohexanecarboxylate

생성물 1

HCID 22167752Methyl trans-4-[(tert-butyldimethylsilyl)oxy]cyclohexanecarboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

5.0 g (32 mmol) of methyl 4-hydroxycyclohexanecarboxylate were initially charged in 100 ml of dimethylformamide. 6.7 g (44 mmol) of tert-butyldimethylsilyl chloride and 4.1 g (60 mmol) of imidazole were then added, and the mixture was stirred at RT for another 14 h. The solvent was removed under reduced pressure and the residue was taken up in 100 ml of methyl tert-butyl ether and 100 ml of saturated aqueous sodium bicarbonate solution. The phases were separated, the organic phase was dried over magnesium sulphate and filtered and the solvent was removed under reduced pressure. Yield: 8.1 g (93% of theory)

후처리

  1. customThe solvent was removed under reduced pressure
  2. customThe phases were separated
  3. dry with materialthe organic phase was dried over magnesium sulphate
  4. filtrationfiltered
  5. customthe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-3fda105d682f4eb2a2319892d602adea
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434690B2

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