Ammonium Chloride → (7-Methoxy-1-benzofuran-2-yl)methanol

HRID 636531Notes

Reaction equation

HRID 636531 reaction equation
C([O:3][C:4]([C:6]1[O:7][C:8]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1)=O)C.[BH4-].[Li+].[Cl-].[NH4+]>O1CCCC1>[OH:3][CH2:4][C:6]1[O:7][C:8]2[C:14]([O:15][CH3:16])=[CH:13][CH:12]=[CH:11][C:9]=2[CH:10]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 521284Ethyl 7-methoxy-1-benzofuran-2-carboxylateHCID 4148881Lithium borohydride

Product 1

HCID 11788606(7-Methoxy-1-benzofuran-2-yl)methanolYield 106.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-ethoxycarbonyl-7-methoxybenzofuran (360 mg), lithium borohydride (36 mg) in tetrahydrofuran (4 ml) was stirred at ambient temperature overnight and then for 8 hours at 50° C. Saturated ammonium chloride solution was added to the reaction mixture, and the solution was extracted with ethyl acetate. The extract was washed with saturated ammonium chloride solution and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (n-hexane—ethyl acetate) to give 2-hydroxymethyl-7-methoxybenzofuran (310 mg).

Workup

  1. waitfor 8 hours at 50° C
  2. extractionthe solution was extracted with ethyl acetate
  3. washThe extract was washed with saturated ammonium chloride solution and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by flash chromatography (n-hexane—ethyl acetate)

Sources & evidence

ORD record
ord-ab28d31b44c34453b0bcce9f953c146e
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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