Sodium borohydride → HCID 54216095, compound

HRID 1165703Notes

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 mol) of the E isomer of 1-chloro-5-(4-chlorophenyl)-2,2-dimethyl-4-(1,2,4-triazol-1-yl)-4-penten-3-one (prepared as described in Example III-3) and 0.467 g (4.11 mmol) of calcium chloride were dissolved in 30 ml of isopropanol, and a solution of 0.167 g (4.3 mmol) of sodium borohydride was added dropwise to the above solution at -5° C. After 6 hours, the reaction mixture was warmed to 25° C. and was 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 oleaginous residue crystallized on stirring it 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

concentrationwas concentrated 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 oleaginous residue crystallized

Sources & evidence

ORD record: ord-71cabaa3824f4d079cc1b1a1cc5acbb7
Source dataset: uspto-grants-1990_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04911750

Reaction notes

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