Water → HCID 70197022, compound

HRID 342427Notes

Reaction equation

HRID 342427 reaction equation
[CH:1]([C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8])=[O:2].[BH4-].[Na+].O>CO>[OH:2][CH2:1][C:3]1[C:4]2[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-:15])=[O:14])[C:5]=2[O:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 867535523-Formyl-2-methyl-7-nitrobenzo[b]furan

Product 1

HCID 70197022HCID 70197022, compoundYield 74.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 3-formyl-2-methyl-7-nitrobenzo[b]furan (1.83 g) and sodium borohydride (200 mg) in methanol (40 ml) was stirred at ambient temperature for 2 hours. The reaction mixture was poured into cold water. The separated oil was extracted with dichloromethane. The extract was washed with brine, dried and evaporated in vacuo. The residue was purified by column chromatography on silica gel to give 3-hydroxymethyl-2-methyl-7-nitrobenzo[b]furan (1.38 g) as a solid.

Workup

  1. extractionThe separated oil was extracted with dichloromethane
  2. washThe extract was washed with brine
  3. customdried
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-37724ab1656547ecbe4ee241eb8c5182
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

Loading…