2,3-Dihydrobenzofuran-5-carboxaldehyde → (2,3-Dihydro-1-benzofuran-5-yl)methanol

HRID 324633Notes

Reaction equation

HRID 324633 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1.[BH4-].[Na+]>CO.O>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][OH:11])=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 7359012,3-Dihydrobenzofuran-5-carboxaldehydeHCID 4311764Sodium borohydride

Product 1

HCID 2776158(2,3-Dihydro-1-benzofuran-5-yl)methanolYield 91%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2,3-dihydrobenzofuran-5-carbaldehyde (30.0 g, 0.202 mol) in methanol (150 mL) was added sodium borohydride (3.83 g, 0.101 mol) under ice-cooling. The mixture was stirred for 15 minutes at ambient temperature and then diluted with water. The product was extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to afford the title compound (yield 27.6 g, 91%) as an oily product.

Workup

  1. temperaturecooling
  2. extractionThe product was extracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-0e7457b7cc7c4102b4b04e499fc06b48
Source dataset
uspto-grants-2001_04
Patent number
US06218429B1

Reaction notes

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