TMS-Imidazole → (4aS,8aR)-5-[(R)-5-Trimethylsilanyloxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-one

HRID 581609노트

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HRID 581609 반응식
[OH:1][C:2]([CH3:21])([CH3:20])[C:3]#[C:4][CH2:5][C@H:6]([C:8]1[C@:9]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][CH:17]=1)[C:13](=[O:18])[CH2:12][CH2:11][CH2:10]2)[CH3:7].[Si:22](C1NC=CN=1)([CH3:25])([CH3:24])[CH3:23]>C(Cl)Cl>[CH3:23][Si:22]([CH3:25])([CH3:24])[O:1][C:2]([CH3:20])([CH3:21])[C:3]#[C:4][CH2:5][C@H:6]([C:8]1[C@:9]2([CH3:19])[C@@H:14]([CH2:15][CH2:16][CH:17]=1)[C:13](=[O:18])[CH2:12][CH2:11][CH2:10]2)[CH3:7]

참가 물질

4

반응물 2

HCID 14420972TMS-ImidazoleHCID 57031123(4aS,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one

생성물 1

HCID 67613097(4aS,8aR)-5-[(R)-5-Trimethylsilanyloxy-1,5-dimethyl-hex-3-ynyl]-4a-methyl-1,2,3,4,4a,7,8,8a-octahydro-naphthalen-1-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

446 mg (1.55 mmol) of (4aS,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-3,4,4a,7,8,8a-hexahydro-2H-naphthalen-1-one in 12 ml of abs. CH2Cl2 was treated with 2.03 ml (9 eq.) of TMS-imidazole and kept at RT for 24 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, 561 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-2a4b6d95962147b2ac4a05cf0cfd6b68
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05919986

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