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

HRID 581614Notes

Reaction equation

HRID 581614 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-6fdf41fdeba148a3ab262632999f25a1
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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