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

HRID 1165700Notes

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 (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

additionThe reaction mixture was thereafter poured onto water
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-520905ef344a483a97d01857a85acf7d
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04911750

Reaction notes

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