Sodium borohydride → HCID 19759235, compound

HRID 1586804Notes

Reaction equation

HRID 1586804 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[C:13]2[C:19]#[N:20])=[CH:8][CH:7]=1)=[O:5])[CH3:2].[BH4-].[Na+]>ClCCCl>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[C:15]([CH2:17][OH:18])[CH:14]=[C:13]2[C:19]#[N:20])=[CH:10][CH:11]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19759475HCID 19759475, compound

Product 1

HCID 19759235HCID 19759235, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 1-(4-ethoxycarbonylphenyl)-4-formylpyrrole-2-carbonitrile (2.0 g) in 1,2-dichloroethane (10 ml) was added sodium borohydride (296 mg) in one portion under nitrogen at ambient temperature. The mixture was stirred for one hour at the same temperature and then quenched with aqueous saturated ammonium chloride solution at 5° C. The organic layer was washed with water and brine, dried, and concentrated in vacuo. The residue was purified by silica gel column chromatography eluted by a mixture of ethyl acetate and n-hexane (2:1) to give 1-(4-ethoxycarbonylphenyl)-4-hydroxymethylpyrrole-2-carbonitrile (1.3 g) as a white solid.

Workup

  1. customquenched with aqueous saturated ammonium chloride solution at 5° C
  2. washThe organic layer was washed with water and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted by a mixture of ethyl acetate and n-hexane (2:1)

Sources & evidence

ORD record
ord-d9da9fe9f1e4454caac7c319d1098224
Source dataset
uspto-grants-1993_06
Patent number
US05215994

Reaction notes

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