Imidazole → HCID 13470490, compound
Reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4]/[CH:5]=[CH:6]\[CH2:7][OH:8].N1C=CN=C1.[Si:14](Cl)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]>CN(C)C=O>[Si:14]([O:8][CH2:7]/[CH:6]=[CH:5]\[CH2:4][CH2:3][CH2:2][Cl:1])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
98 g of 6-chlorohex-2Z-en-1-ol was dissolved in 250 ml of dimethylformamide and treated with 68 g of imidazole and 113 g of t-butyldimethylsilyl chloride. After stirring 1.5 hours at room temperature, the reaction mixture was poured into ice water and extracted twice with 300 ml of ether. The ethereal solution was washed with 5% hydrochloric acid, aqueous sodium bicarbonate and brine. After drying over potassium carbonate the solvent was evaporated and the residue distilled to give 168.1 g of 6-chlorohex-2Z-en-1-ol t-butyldimethylsilyl ether, bp 95°-100° C./0.4 mm.