Hydrochloric Acid → Benzofuran-6-ylmethanol

HRID 2118106Notes

Reaction equation

HRID 2118106 reaction equation
[O:1]1[C:5]2[CH:6]=[C:7]([C:10](OC)=[O:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.Cl>C1COCC1>[O:1]1[C:5]2[CH:6]=[C:7]([CH2:10][OH:11])[CH:8]=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22481705Methyl 6-benzofurancarboxylate

Product 1

HCID 59010054Benzofuran-6-ylmethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 1-benzofuran-6-carboxylate (J. Med. Chem. 1995, 38, 3094; 142 mg, 0.8 mmol) in THF (5 ml) was added dropwise to a stirred suspension of lithium aluminum hydride (92 mg, 2.4 mmol) in THF (2 mL) at −10° C. The mixture was stirred at room temperature for 30 min, cooled to 0° C. and treated slowly with water (1 mL). The mix was brought to pH 1 with 2N HCl and extracted with ethyl acetate (3×). The combined extracts were washed with water, brine, dried (MgSO4) and concentrated to give the final product.

Workup

  1. temperaturecooled to 0° C.
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined extracts were washed with water, brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5e964f9a6e754acb99afc89d1f082d9e
Source dataset
uspto-grants-2008_10
Patent number
US07442808B2

Reaction notes

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