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

HRID 1252327Notes

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-d159d3e9b8274e0d84704d00d141183c
Source dataset: uspto-grants-1988_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04743293

Reaction notes

Loading…