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 581609Notes

Reaction equation

HRID 581609 reaction equation
[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]

Participants

4

Reactant 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

Product 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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.

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-2a4b6d95962147b2ac4a05cf0cfd6b68
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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