Lithium borohydride → HCID 19759464, compound

HRID 248376Notes

Reaction equation

HRID 248376 reaction equation
C([O:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[C:15]([CH:17]=[CH2:18])[CH:14]=[C:13]2[C:19]#[N:20])=[CH:8][CH:7]=1)=O)C.[BH4-].[Li+]>O1CCCC1>[OH:3][CH2:4][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[CH:16]=[C:15]([CH:17]=[CH2:18])[CH:14]=[C:13]2[C:19]#[N:20])=[CH:10][CH:11]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydride2×HCID 19759261HCID 19759261, compound

Product 1

HCID 19759464HCID 19759464, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1-(4-ethoxycarbonylphenyl)-4-vinylpyrrole- 2-carbonitrile (1.59 g) and lithium borohydride (78.4 mg) in tetrahydrofuran (30 ml) was refluxed for 3 hours. To the pale green solution was added lithium borohydride (78.4 mg) and the mixture was refluxed for 3 hours. The cooled mixture was quenched with saturated aqueous ammonium chloride solution and diethyl ether was added. The separated organic layer was washed with saturated aqueous ammonium chloride solution, dried, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted by 2% methanol in dichloromethane to yield 1-(4-hydroxymethylphenyl)-4-vinylpyrrole-2-carbonitrile (910 mg) as a white solid.

Workup

  1. temperaturewas refluxed for 3 hours
  2. temperaturethe mixture was refluxed for 3 hours
  3. customThe cooled mixture was quenched with saturated aqueous ammonium chloride solution and diethyl ether
  4. additionwas added
  5. washThe separated organic layer was washed with saturated aqueous ammonium chloride solution
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel
  9. washeluted by 2% methanol in dichloromethane

Sources & evidence

ORD record
ord-b8e43a10db7a40f88faac0bc996b5a06
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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