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

HRID 56827ノート

反応式

HRID 56827 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-3fda105d682f4eb2a2319892d602adea
出典データセット
uspto-grants-2016_09
特許番号
US09434690B2

反応ノート

読み込み中…