2,3-Dihydro-1-benzofuran-7-carboxylic acid → (2,3-Dihydro-1-benzofuran-7-yl)methanol

HRID 878653Notes

Reaction equation

HRID 878653 reaction equation
[O:1]1[C:5]2[C:6]([C:10](O)=[O:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1>C1COCC1>[O:1]1[C:5]2[C:6]([CH2:10][OH:11])=[CH:7][CH:8]=[CH:9][C:4]=2[CH2:3][CH2:2]1

Participants

3

Reactant 1

HCID 27950142,3-Dihydro-1-benzofuran-7-carboxylic acid

Product 1

HCID 2795020(2,3-Dihydro-1-benzofuran-7-yl)methanolYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Added BH3 (1M in THF, 9 mL) to a solution of 2,3-dihydro-1-benzofuran-7-carboxylic acid (481 mg, 2.93 mmol) in THF (7 mL) drop wise at 0° C., thereto, the mixture was stirred at room temperature overnight. Extracted with ethyl acetate twice, and washed the organic phase with brine and dried with anhydrous Na2SO4, concentrated to give the title compound (340 mg, 77%). 1H NMR (400 MHz, CDCl3): δ 2.09 (1H, s), 3.22 (2H, t, J=8.8 Hz), 4.61 (2H, t, J=8.8 Hz), 4.67 (2H, s), 6.83 (1H, t, J=7.6 Hz), 7.08 (1H, d, J=7.2 Hz), 7.14 (1H, d, J=7.2 Hz).

Workup

  1. extractionExtracted with ethyl acetate twice
  2. washwashed the organic phase with brine
  3. dry with materialdried with anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-c7896538a4f948978dcaf7195f04c336
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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