HCID 15643782, compound → HCID 54146363, compound

HRID 342431Notes

Reaction equation

HRID 342431 reaction equation
[C:1]([C:4]1[C:9]2[O:10][C:11]([CH3:14])=[C:12]([CH3:13])[C:8]=2[CH:7]=[CH:6][CH:5]=1)(O)=[O:2]>O1CCCC1>[CH3:14][C:11]1[O:10][C:9]2[C:4]([CH2:1][OH:2])=[CH:5][CH:6]=[CH:7][C:8]=2[C:12]=1[CH3:13]

Participants

3

Reactant 1

HCID 15643782HCID 15643782, compound

Product 1

HCID 54146363HCID 54146363, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-carboxy-2,3-dimethylbenzo[b]furan (400 mg) and borane-dimethyl sulfide complex (0.4 ml) in tetrahydrofuran (6 ml) was stirred at ambient temperature for 40 hours. The mixture was quenched with 1N-hydrochloric acid and extracted with dichloromethane. The extract was washed with brine, dried over sodium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel and the obtained oil was crystallized from n-hexane to give 2,3-dimethyl-7-hydroxymethylbenzo[b]furan (322 mg).

Workup

  1. customThe mixture was quenched with 1N-hydrochloric acid
  2. extractionextracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by column chromatography on silica gel
  7. customthe obtained oil was crystallized from n-hexane

Sources & evidence

ORD record
ord-02ce1a48474041a5b1b1b706e1c57ede
Source dataset
uspto-grants-1999_01
Patent number
US05858995

Reaction notes

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