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

HRID 1905588Notes

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

Conditions

Temperature: 70 °C

Procedure

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 (Example 2) in 100 ml of acetic anhydride. The mixture was stirred at 70° C. for 4 hours. Thereafter, the reaction mixture was poured onto water and neutralised 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 pale yellow oil.

Workup

extractionThe aqueous phase was extracted several times with ether
dry with materialThe combined ether phases were dried over sodium sulphate
concentrationconcentrated

Sources & evidence

ORD record: ord-6c6ad5c5c1a04a17a3cf2e5be5332e31
Source dataset: uspto-grants-1987_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04647302

Reaction notes

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