TMS-Imidazole → (4aR,5R,8aR)-5-((R)-1,5-Dimethyl-5-trimethylsilanyloxy-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one

HRID 581614

반응식

HRID 581614 반응식
[OH:1][C:2]([CH3:21])([CH3:20])[C:3]#[C:4][CH2:5][C@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH3:7].[Si:22](C1NC=CN=1)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[CH3:7][C@@H:6]([C@H:8]1[CH2:17][CH2:16][CH2:15][C@@H:14]2[C@:9]1([CH3:19])[CH2:10][CH2:11][CH2:12][C:13]2=[O:18])[CH2:5][C:4]#[C:3][C:2]([CH3:20])([O:1][Si:22]([CH3:25])([CH3:24])[CH3:23])[CH3:21]

참가 물질

4

반응물 2

HCID 14420972TMS-ImidazoleHCID 56998139(4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one

생성물 1

HCID 54264802(4aR,5R,8aR)-5-((R)-1,5-Dimethyl-5-trimethylsilanyloxy-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one수율 93%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

860 mg (2.96 mmol) of (4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one in 23 ml of abs. CH2Cl2 was treated with 3.89 ml (26.6 mmol) of TMS-imidazole and kept at RT for 4 h. Pouring onto crushed ice, twofold extraction with ether, washing with water and brine, and drying over sodium sulfate left a crude product, which was purified by flash chromatography (SiO2, hexane/AcOEt=9/1). Thereby, 998 mg of the title compound was obtained as colorless oil.

후처리

  1. additionPouring
  2. customonto crushed
  3. extractionice, twofold extraction with ether
  4. washwashing with water and brine
  5. dry with materialdrying over sodium sulfate
  6. waitleft a crude product, which
  7. customwas purified by flash chromatography (SiO2, hexane/AcOEt=9/1)

출처 및 근거

ORD 기록
ord-6fdf41fdeba148a3ab262632999f25a1
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919986

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