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

HRID 581614

反応式

HRID 581614 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-6fdf41fdeba148a3ab262632999f25a1
出典データセット
uspto-grants-1999_07
特許番号
US05919986

関連ノート

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