Imidazole → HCID 12742151, compound

HRID 1731648Notes

Reaction equation

HRID 1731648 reaction equation
[CH:1]1([OH:7])[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.N1C=CN=C1.[C:13]([Si:17](Cl)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([CH3:16])([CH3:15])[CH3:14]>CN(C)C=O>[Si:17]([O:7][CH:1]1[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1)([C:13]([CH3:16])([CH3:15])[CH3:14])([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 131982-Cyclohexen-1-OLHCID 94078tert-Butyldiphenylchlorosilane

Product 1

HCID 12742151HCID 12742151, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 g of 2-cyclohexen-1-ol, 7.6 g of imidazole and 14.6 ml of tert-butylchlorodiphenylsilane in 100 ml of N,N-dimethylformamide was stirred at room temperature for 16 hrs. The mixture was then partitioned between 100 ml of saturated brine and 250 ml of ether. The layers were separated and the organic layer was washed with 100 ml of water and dried over magnesium sulfate and the solvent was evaporated in vacuo to give 3-(tert-butyldiphenylsilyloxy)cyclohexene as a viscous oil which was used without further purification. 1H NMR (CDCl3) δ 1.05 (s, 9H); 4.10 (m, 1H); 5.50 (br s, 2H); 7.20-7.70 (m, 10H).

Workup

  1. customThe mixture was then partitioned between 100 ml of saturated brine and 250 ml of ether
  2. customThe layers were separated
  3. washthe organic layer was washed with 100 ml of water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-233e4ba08f1d4dcf9f9cd2f2061b89b7
Source dataset
uspto-grants-1986_11
Patent number
US04622422

Reaction notes

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