Pyridine → 3-Acetoxy-1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-ene

HRID 1262470Notes

Reaction equation

HRID 1262470 reaction equation
N1[CH:6]=[CH:5]C=CC=1.[CH:7]1([CH:13]=[C:14]([N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH:15]([OH:20])[C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(=O)(O)[O-:27].[Na+]>C(OC(=O)C)(=O)C>[C:5]([O:20][CH:15]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:14]([N:21]1[CH:25]=[N:24][CH:23]=[N:22]1)=[CH:13][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1)(=[O:27])[CH3:6]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1148141-Cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-olHCID 516892Sodium Bicarbonate

Product 1

HCID 541846513-Acetoxy-1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-eneYield 70.8%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 13.15 g (0.05 mol) of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol (prepared as described in Example II-2) in 50 ml of dioxane was added dropwise to a suspension of 1.5 g of 80% strength sodium hydride in 50 ml of dioxane. After the evolution of hydrogen had ceased, 3.9 g (0.05 mol) of acetyl chloride were added dropwise to the mixture. The mixture was heated under reflux for 4 hours. After the mixture had cooled, the solvent was distilled off in vacuo, and the residue was taken up in methylene chloride and the solution was extracted with water. The organic phase was dried over sodium sulphate and filtered, and the solution was concentrated. The residue was purified over a column (silica gel; methanol: chloroform=1:3). 5.6 g (35.4% of theory) of 3-acetoxy-1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-ene were obtained as a slightly yellow oil. 2 ml of pyridine were added to a solution of 13.15 g (0.05 mol) of 1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-en-3-ol (prepared as described in Example II-2) in 100 ml of acetic anhydride. The mixture was stirred for four hours at 70° C. The reaction mixture was thereafter poured onto water and was neutralized with sodium bicarbonate. The aqueous phase was extracted several times with ether. The combined ether phases were dried over sodium sulphate and concentrated. 11.2 g (70.8% of theory) of 3-acetoxy-1-cyclohexyl-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-pent-1-ene were obtained as a slightly yellow oil.

Workup

  1. additionThe reaction mixture was thereafter poured onto water
  2. extractionThe aqueous phase was extracted several times with ether
  3. dry with materialThe combined ether phases were dried over sodium sulphate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-1ab0fe16dccd433a9fea68fb9f657e3f
Source dataset
uspto-grants-1984_06
Patent number
US04452625

Reaction notes

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