Water → HCID 73183738, compound

HRID 1980218Notes

Reaction equation

HRID 1980218 reaction equation
[OH:1][C:2]([CH3:21])([CH3:20])[CH:3]([CH3:19])[CH:4]=[CH:5][CH:6]([CH:8]1[C:16]2([CH3:17])[CH:11]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)[CH3:7].[CH3:22][Si:23]([CH3:30])([CH3:29])N1C=CN=C1.O>C(Cl)Cl>[CH3:7][CH:6]([CH:8]1[C:16]2([CH3:17])[CH:11]([C:12](=[O:18])[CH2:13][CH2:14][CH2:15]2)[CH2:10][CH2:9]1)[CH:5]=[CH:4][CH:3]([CH3:19])[C:2]([CH3:20])([O:1][Si:23]([CH3:30])([CH3:29])[CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 28925(Trimethylsilyl)imidazoleHCID 73117296HCID 73117296, compound

Product 1

HCID 73183738HCID 73183738, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 200.0 mg (0.679 mmol) of [1R-[1α-(1R*,2E,4S*),3aβ,7aα]]-octahydro-1-(5-hydroxy-1,4,5-trimethyl-2-hexenyl)-7a-methyl-4H-inden-4-one in 10 mL of dry methylene chloride was treated with 0.4 mL (2.726 mmol) of N-(trimethylsilyl)imidazole and the resulting mixture stirred at room temperature, under argon, for 18 hours. It was then treated with 1 mL of water, stirred for an additional 30 minutes then diluted with methylene chloride. The organic phase was separated, washed with water and brine, dried and evaporated to dryness. The residue obtained was purified by rapid filtration through a short silica gel column, eluted with hexane-ethyl acetate (5:1) to give 214.0 mg (84% yield) of pure [1R-[1α-(1R*,2E,4S*),3aβ,7aα]]-octahydro-1-(1,4,5-trimethyl-5-trimethylsilyloxy-2-hexenyl)-7a-methyl-4H-inden-4-one, as a thick, colorless oil.

Workup

  1. stirringstirred for an additional 30 minutes
  2. customThe organic phase was separated
  3. washwashed with water and brine
  4. customdried
  5. customevaporated to dryness
  6. customThe residue obtained
  7. filtrationwas purified by rapid filtration through a short silica gel column
  8. washeluted with hexane-ethyl acetate (5:1)

Sources & evidence

ORD record
ord-0e4f51177b5e43b9a6db55ad546edce8
Source dataset
uspto-grants-1985_04
Patent number
US04508651

Reaction notes

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