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

HRID 3142

반응식

HRID 3142 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

반응 조건

온도
25 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-b0f251ba8a8b43138ec22405d9b99942
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05733882

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