Sodium borohydride → HCID 19804291, compound

HRID 1681847Notes

Reaction equation

HRID 1681847 reaction equation
[BH4-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10](=[O:26])/[C:11](/[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1>CO>[Cl:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH:10]([OH:26])/[C:11](/[C:19]1[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=1)=[CH:12]/[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19804293HCID 19804293, compound

Product 1

HCID 19804291HCID 19804291, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

7.6 g (0.20 mol) of sodium borohydride were added a little at a time, at 0° C., to a solution of 33.75 g (0.10 mol) of the E-1-(2-chlorophenyl)-2-(4-fluorophenyl)-3-(3-pyridyl)-2-propen-1-one, prepared under 2.), in 500 ml of methanol. Stirring was carried out for 2 hours at 0° C., excess sodium borohydride was destroyed by the dropwise addition of acetic acid and the mixture was evaporated down under reduced pressure. The residue was taken up in a water/dichloromethane mixture, and the organic phase was washed with water, dried over sodium sulfate and evaporated down under reduced pressure. Trituration with 9:1 methyl tert-butyl ether/pentane gave 27.0 g (79% of theory) of crystalline product of melting point 82°-83°C.(cf. Table, Example No. 682).

Workup

  1. customexcess sodium borohydride was destroyed by the dropwise addition of acetic acid
  2. customthe mixture was evaporated down under reduced pressure
  3. washthe organic phase was washed with water
  4. dry with materialdried over sodium sulfate
  5. customevaporated down under reduced pressure
  6. customTrituration with 9:1 methyl tert-butyl ether/pentane gave 27.0 g (79% of theory) of crystalline product of melting point 82°-83°C.(cf. Table, Example No. 682)

Sources & evidence

ORD record
ord-773673e12cfc42309da5ea74a1d6c3e7
Source dataset
uspto-grants-1992_12
Patent number
US05175167

Reaction notes

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