Water → 7-Methoxy-2-methylbenzofuran

HRID 636532Notes

Reaction equation

HRID 636532 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

Sources & evidence

ORD record
ord-99fd776611a84181b7ae07d92a263e0e
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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