Imidazole → (trans)-2-(t-Butyldimethysiloxy)-cyclopentanol

HRID 3142

反応式

HRID 3142 の反応式
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[C@@H:14]1([OH:20])[CH2:18][CH2:17][CH2:16][C@H:15]1[OH:19]>CN(C=O)C>[O:19]([C@@H:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[OH:20])[Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 225711trans-1,2-Cyclopentanediol

生成物 1

HCID 70100529(trans)-2-(t-Butyldimethysiloxy)-cyclopentanol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
25 °C

実験手順

To a mixture of t-butyldimethylsilyl chloride (5.08 g, 33.7 mmol) and imidazole (2.30 g, 33.7 mmol) in DMF (10 mL), a solution of trans-1,2-cyclopentanediol in DMF (4 mL) was added. The reaction mixture was stirred overnight at 25° C. The reaction mixture was diluted with ice water and extracted with ether. The ether extract was washed with water and brine, dried over magnesium sulfate, filtered and the solvent removed in vacuo. The residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%).

後処理

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customThe residue was purified by flash chromatography (silica, 9:1 hexane:ethyl acetate) to the title compound as an oil (3.44 g, 49%)

出典と根拠

ORDレコード
ord-b0f251ba8a8b43138ec22405d9b99942
出典データセット
uspto-grants-1998_03
特許番号
US05733882

関連ノート

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