TMS-Imidazole → (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one

HRID 1604835

反応式

HRID 1604835 の反応式
[OH:1][C:2]([CH3:23])([CH3:22])/[CH:3]=[CH:4]/[CH:5]=[CH:6]/[CH2:7][C@H:8]([C@H:10]1[CH2:19][CH2:18][CH2:17][C@@H:16]2[C@:11]1([CH3:21])[CH2:12][CH2:13][CH2:14][C:15]2=[O:20])[CH3:9].[Si:24](C1NC=CN=1)([CH3:27])([CH3:26])[CH3:25]>C(Cl)Cl>[CH3:9][C@@H:8]([C@H:10]1[CH2:19][CH2:18][CH2:17][C@@H:16]2[C@:11]1([CH3:21])[CH2:12][CH2:13][CH2:14][C:15]2=[O:20])[CH2:7]/[CH:6]=[CH:5]/[CH:4]=[CH:3]/[C:2]([CH3:22])([O:1][Si:24]([CH3:27])([CH3:26])[CH3:25])[CH3:23]

参加物

4

反応物 2

HCID 14420972TMS-ImidazoleHCID 86754888(4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-octahydro-naphthalen-1-one

生成物 1

HCID 86754887(4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

323 mg of (4aR,5R,8aR)-5-((3E,5E)-(R)-7-hydroxy-1,7-dimethyl-octa-3,5-dienyl)-4a-methyl-octahydro-naphthalen-1-one, was reacted at 40° with 1.33 ml of TMS-imidazole (9 equivalents) in 8 ml of CH2Cl2. After a few hours the mixture was poured onto crushed ice, extracted with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=9/1) yielded 326 mg of (4aR,5R,8aR)-5-[(3E,5E)-(R)-(1,7-dimethyl-7-trimethylsilanyloxy-octa-3,5-dienyl)]-4a-methyl-octahydro-naphthalen-1-one as colourless oil.

後処理

  1. additionAfter a few hours the mixture was poured
  2. customonto crushed ice
  3. extractionextracted with ether
  4. washwashed with water
  5. dry with materialdried over sodium sulfate
  6. customevaporated to dryness

出典と根拠

ORDレコード
ord-a4756f5bf9f944ceb0f4c7886654674e
出典データセット
uspto-grants-1999_11
特許番号
US05994569

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