Water → HCID 23510333, compound

HRID 1883171Notes

Reaction equation

HRID 1883171 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2)O.[BH4-].[Na+].O>CC(O)C>[N:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:17]=[C:8]([CH2:6][C:2]2[NH:1][CH:5]=[CH:4][CH:3]=2)[CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 23510482HCID 23510482, compound

Product 1

HCID 23510333HCID 23510333, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a solution of (1H-pyrrol-2-yl)(3-quinolyl)methanol (40.0 mg) in 2-propanol (3 mL) was added sodium borohydride (33.9 mg), and the mixture was refluxed for one hour. To the mixture was added water, and the mixture was concentrated. The residue was separated using water and ethyl acetate, and the organic layer was dried, filtered, and concentrated. The residue was purified by silica gel column chromatography to give 2-(3-quinolylmethyl)-1H-pyrrole (30.0 mg, 75%).

Workup

  1. temperaturethe mixture was refluxed for one hour
  2. concentrationthe mixture was concentrated
  3. customThe residue was separated
  4. customthe organic layer was dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b0e6c19112ab4aa398fd77f2d5353f69
Source dataset
uspto-grants-2004_07
Patent number
US06759429B2

Reaction notes

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