Cornforth reagent → (4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-one

HRID 581613Notes

Reaction equation

HRID 581613 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@@H:13]2[OH:18])[CH3:7].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[OH:1][C:2]([CH3:20])([CH3:21])[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]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 57216772(1S,4aR,5R,8aR)-5-((R)-5-Hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol

Product 1

HCID 56998139(4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-octahydro-naphthalen-1-oneYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.22 g (4.17 mmol) of (1S,4aR,5R,8aR)-5-((R)-5-hydroxy-1,5-dimethyl-hex-3-ynyl)-4a-methyl-decahydro-naphthalen-1-ol was dissolved in 36 ml of abs. CH2Cl2 and oxidized with 4.72 g (12.51 mmol) of pyridinium dichromate during 2 h at ambient temperature. Filtration overCelite, evaporation to dryness, and flash chromatography (SiO2, Hexane/AcOEt=7/3) produced 860 mg of the title compound as colorless oil.

Workup

  1. filtrationFiltration overCelite, evaporation to dryness, and flash chromatography (SiO2, Hexane/AcOEt=7/3)

Sources & evidence

ORD record
ord-d25ec022b26f4318aa2de627382100bf
Source dataset
uspto-grants-1999_07
Patent number
US05919986

Reaction notes

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