Sodium borohydride → HCID 54216095, compound

HRID 568751Notes

Reaction equation

[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[C:4](=[O:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][CH:8]=1.[Cl-].[Ca+2].[Cl-].[BH4-].[Na+]>C(O)(C)C>[Cl:1][CH2:2][C:3]([CH3:21])([CH3:20])[CH:4]([OH:19])[C:5]([N:14]1[CH:18]=[N:17][CH:16]=[N:15]1)=[CH:6][C:7]1[CH:8]=[CH:9][C:10]([Cl:13])=[CH:11][CH:12]=1

Participants

Conditions

Temperature: 25 °C

Procedure

2.0 g (6.13 moles) of the E-isomer of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-one (the compound of Example 2) and 0.467 g (4.11 mmoles) of calcium chloride were dissolved in 30 ml of isopropanol, and a solution of 0.167 g (4.3 mmoles) of sodium borohydride was added dropwise at -5° C. After 6 hours, the reaction mixture was warmed to 25° C. and concentrated in vacuo. The residue was poured onto water and the mixture was extracted with ethyl acetate. The combined ethyl acetate extracts were dried over sodium sulphate and concentrated in vacuo. The oily residue crystallised on trituration with diisopropyl ether. 1.1 g (55% of theory) of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-ol of melting point 170° C. were obtained as the E-isomer.

Workup

concentrationconcentrated in vacuo
additionThe residue was poured onto water
extractionthe mixture was extracted with ethyl acetate
dry with materialThe combined ethyl acetate extracts were dried over sodium sulphate
concentrationconcentrated in vacuo
customThe oily residue crystallised on trituration with diisopropyl ether

Sources & evidence

ORD record: ord-5d54997165ed4de08f83b83cabba304a
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04729783

Reaction notes

Loading…