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

Reaction equation

HRID 1604835 reaction equation
[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]

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-a4756f5bf9f944ceb0f4c7886654674e
Source dataset
uspto-grants-1999_11
Patent number
US05994569

Linked notes

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