Sodium borohydride → HCID 20187544, compound

HRID 542506Notes

Reaction equation

HRID 542506 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH:10]([F:16])[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1.[BH4-].[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH:9]([OH:17])[CH:10]([F:16])[N:11]1[CH:15]=[N:14][CH:13]=[N:12]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 20187539HCID 20187539, compound

Product 1

HCID 20187544HCID 20187544, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a suspension of 2.4 g of 1-(2,4-dichlorophenyl)-2-fluoro-2-(1H-1,2,4-triazol-1-yl)ethanone in 9.5 ml of methanol and 0.5 ml of water is added at 5°-10° C., with stirring, 0.12 g of sodium borohydride, and the resulting mixture is stirred firstly for 1 hour at 0°-5° C. and then for 2 hours at room temperature, in the course of which a clear solution gradually forms. This solution is then poured into ice-water, and the mixture is extracted twice with dichloromethane. The combined extracts are dried over sodium sulfate, filtered, and concentrated by evaporation. The residue is distilled under high vacuum to obtain the above alcohol as a diastereoisomeric mixture; b.p. of the crude product: 150°-160° C./0.07 mbar. Crystallisation from diethyl ether/diisopropyl ether yields the purified diastereoisomeric mixture in the form of beige crystals; melting range 103°-112° C.

Workup

  1. additionis added at 5°-10° C.
  2. extractionthe mixture is extracted twice with dichloromethane
  3. dry with materialThe combined extracts are dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated by evaporation
  6. distillationThe residue is distilled under high vacuum

Sources & evidence

ORD record
ord-ee7a117baa5140d798e0f0bc437d1590
Source dataset
uspto-grants-1987_04
Patent number
US04657921

Reaction notes

Loading…