Sodium borohydride → HCID 86746832, compound

HRID 248382Notes

Reaction equation

HRID 248382 reaction equation
C(OC(C1C=CC([N:12]2[CH:16]=[C:15]([CH:17]=[O:18])[CH:14]=[C:13]2[C:19]#[N:20])=CC=1)=O)C.[BH4-].[Na+]>ClCCCl>[OH:18][CH2:17][C:15]1[CH:14]=[C:13]([C:19]#[N:20])[NH:12][CH:16]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 19759475HCID 19759475, compound

Product 1

HCID 86746832HCID 86746832, compoundYield 142.8%

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 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-56430e99099d45e2a590c5bec9173100
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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