Cornforth reagent → 5-Hexynoic acid, 6-(trimethylsilyl)-

HRID 745898Notes

Reaction equation

HRID 745898 reaction equation
[CH3:1][Si:2]([CH3:11])([CH3:10])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=[O:13].[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>CN(C)C=O>[CH3:11][Si:2]([CH3:1])([CH3:10])[C:3]#[C:4][CH2:5][CH2:6][CH2:7][C:8]([OH:13])=[O:9]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 10877568HCID 10877568, compound

Product 1

HCID 119900745-Hexynoic acid, 6-(trimethylsilyl)-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 10 gm of 6-trimethylsilylhex-5-ynol in 400 ml of dry dimethylformamide, was added 98 gm of pyridinium dichromate. The solution was stirred in the dark for 24 hours and then partitioned between ether and water. The ether extract was dried over magnesium sulphate and evaporated to an oil. Distillation gave the title compound, b.p. 121°-124° C. (1 mm Hg), IR: 3290, 2162, 1720 cm-1.

Workup

  1. custompartitioned between ether and water
  2. extractionThe ether extract
  3. dry with materialwas dried over magnesium sulphate
  4. customevaporated to an oil
  5. distillationDistillation

Sources & evidence

ORD record
ord-94a3155bf4c94a56a5fec4c02fd5c92a
Source dataset
uspto-grants-1986_07
Patent number
US04602006

Reaction notes

Loading…