Imidazole → HCID 20565023, compound

HRID 1856348Notes

Reaction equation

HRID 1856348 reaction equation
[CH2:1]([C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].N1C=CN=[CH:12]1.Cl[SiH:17]([CH3:19])[CH3:18]>CN(C=O)C>[CH2:1]([C:4]1([O:10][Si:17]([CH3:19])([CH3:12])[CH3:18])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 66108ChlorodimethylsilaneHCID 879381-(2-Propynyl)cyclohexan-1-ol

Product 1

HCID 20565023HCID 20565023, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 55.4 g of 1-(2-propyn-1-yl)cyclohexanol [H. Gutmann, et. al., Helv. Chim. Acta, 42, 719 (1959)] and 79 g of imidazole in 240 ml of DMF at 10° C. initially is added 56 ml of chlorodimethylsilane during 10 minutes. The cloudy yellow solution is stirred at room temperature for 26 hours. The resulting mixture is partitioned between 1000 ml of hexane and 400 ml of water at 0°-5° C. The hexane phase is washed successively with 6×200 ml of cold water and 200 ml of brine. The extract is dried over magnesium sulfate, filtered, and evaporated to give 85 g of colorless liquid, i.r. (film): 1240 and 830 cm-1 (trimethylsilyloxy group).

Workup

  1. customThe resulting mixture is partitioned between 1000 ml of hexane and 400 ml of water at 0°-5° C
  2. washThe hexane phase is washed successively with 6×200 ml of cold water and 200 ml of brine
  3. dry with materialThe extract is dried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-6a8e08532b7b44e88afcdb02966f0094
Source dataset
uspto-grants-1980_08
Patent number
US04218566

Reaction notes

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