Water → 7-Methoxy-2-methylbenzofuran

HRID 2287608Notes

Reaction equation

HRID 2287608 reaction equation
O[CH2:2][C:3]1[O:4][C:5]2[C:11]([O:12][CH3:13])=[CH:10][CH:9]=[CH:8][C:6]=2[CH:7]=1.C([BH3-])#N.[Na+].C(Cl)(Cl)Cl.O>ClC(Cl)C.[I-].[Zn+2].[I-]>[CH3:13][O:12][C:11]1[C:5]2[O:4][C:3]([CH3:2])=[CH:7][C:6]=2[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 5003444Sodium cyanoborohydrideHCID 11788606(7-Methoxy-1-benzofuran-2-yl)methanol

Product 1

HCID 112751777-Methoxy-2-methylbenzofuranYield 34.8%

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of 2-hydroxymethyl-7-methoxybenzofuran (300 mg), sodium cyanoborohydride (796 mg) and zinc iodide (809 mg) in dichloroethane (10 ml) was stirred for 2 hours at ambient temperature and then refluxed overnight. Chloroform and water were added to the reaction mixture, and the separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (n-hexane:ethyl acetate 15:1, v/v) to give 7-methoxy-2-methylbenzofuran (95 mg).

Workup

  1. temperaturerefluxed overnight
  2. washthe separated organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (n-hexane:ethyl acetate 15:1

Sources & evidence

ORD record
ord-51df85549c804e3d828bc348cfefdfcf
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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