Potassium Carbonate → (5-(Difluoromethyl)furan-2-yl)methanol

HRID 560564Notes

Reaction equation

HRID 560564 reaction equation
C(=O)([O-])[O-].[K+].[K+].C([O:10][CH2:11][C:12]1[O:13][C:14]([CH:17]([F:19])[F:18])=[CH:15][CH:16]=1)(=O)C>CO>[F:18][CH:17]([F:19])[C:14]1[O:13][C:12]([CH2:11][OH:10])=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 53728052(5-(Difluoromethyl)furan-2-yl)methyl acetate

Product 1

HCID 20079677(5-(Difluoromethyl)furan-2-yl)methanolYield 96%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of potassium carbonate in anhydrous methanol (10%, 50 mL) was added (5-(difluoromethyl)furan-2-yl)methyl acetate (4.21 g, 22.16 mmol). The reaction mixture was stirred at ambient temperature for 20 minutes, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (3/7) to afford (5-(difluoromethyl)furan-2-yl)methanol as a yellow oil in 96% yield (3.15 g): 1H NMR (300 MHz, CDCl3) δ 6.55 (t, JH-F=54.2 Hz, 1H), 6.58-6.55 (m, 1H), 6.34-6.26 (m, 1H), 4.59 (d. J=5.9 Hz, 2H).

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by column chromatography
  4. washeluted with ethyl acetate/hexane (3/7)

Sources & evidence

ORD record
ord-bc41e2476d0c4d1d91622ffa9a7097f9
Source dataset
uspto-grants-2011_11
Patent number
US08063084B2

Reaction notes

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