Imidazole → HCID 13470490, compound

HRID 462385Notes

Reaction equation

HRID 462385 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

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 13445192HCID 13445192, compound

Product 1

HCID 13470490HCID 13470490, compoundYield 92.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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.

Workup

  1. extractionextracted twice with 300 ml of ether
  2. washThe ethereal solution was washed with 5% hydrochloric acid, aqueous sodium bicarbonate and brine
  3. dry with materialAfter drying over potassium carbonate the solvent
  4. customwas evaporated
  5. distillationthe residue distilled

Sources & evidence

ORD record
ord-1cd5dcebebec42488293ffe2e70f7379
Source dataset
uspto-grants-1985_05
Patent number
US04515727

Reaction notes

Loading…