Water → 7-Methoxy-2,3-dihydrobenzofuran-3-ol

HRID 2176993Notes

Reaction equation

HRID 2176993 reaction equation
[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][C:8](=[O:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1.[BH4-].[Na+].O.[Cl-].[NH4+]>CO>[CH3:1][O:2][C:3]1[C:11]2[O:10][CH2:9][CH:8]([OH:12])[C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 28181127-Methoxybenzofuran-3(2H)-oneHCID 4311764Sodium borohydride

Product 1

HCID 657214207-Methoxy-2,3-dihydrobenzofuran-3-olYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cold (ice water) solution of 7-methoxy-3-(2H)-benzofuranone (846 mg; 5.0 mmol) in methanol (5 mL) is added sodium borohydride (179 mg; 5.0 mmol) is stirred for 15 minutes. Water (5 mL) is added to the solution and stirred 15 minutes. Saturated ammonium chloride (20 mL) is added and the solution is extracted with ethyl acetate. The organics are separated and dried over magnesium sulfate. The solvent is removed to give 831 milligrams of 7-methoxy-2,3-dihydrobenzofuran-3-ol.

Workup

  1. stirringstirred 15 minutes
  2. extractionthe solution is extracted with ethyl acetate
  3. customThe organics are separated
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent is removed

Sources & evidence

ORD record
ord-5e9d790780ab4d8b98fd697276a88ef5
Source dataset
uspto-grants-2015_06
Patent number
US09067897B2

Reaction notes

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