Cornforth reagent → 5-Hexynoic acid, 6-(trimethylsilyl)-
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
Product 1
Reagents, catalysts & solvents 1
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
- custompartitioned between ether and water
- extractionThe ether extract
- dry with materialwas dried over magnesium sulphate
- customevaporated to an oil
- distillationDistillation
Sources & evidence
- ORD record
- ord-94a3155bf4c94a56a5fec4c02fd5c92a
- Source dataset
- uspto-grants-1986_07
- Patent number
- US04602006
Reaction notes
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