Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate → HCID 54073356, compound

HRID 843178Notes

Reaction equation

HRID 843178 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].[F:17][B-](F)(F)F.F[N+]1C(Cl)=CC=CC=1Cl>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][C:13]([F:17])=[C:12]([OH:16])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 748649Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylateHCID 27373072,6-Dichloro-1-fluoropyridiniumtetrafluoroborate

Product 1

HCID 54073356HCID 54073356, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (Joseph G. Atkinson et al., European patent application 0146243 (1985)) (700 mg) in dichloromethane (20 ml) was added 1-fluoro-2,6-dichloropyridinium tetrafluoroborate (807 mg) at room temperature and the mixture was stirred overnight. The reaction was quenched by the addition of water (10 ml), extracted with ethyl acetate (20 ml), washed with brine and dried over anhydrous magnesium sulfate. The mixture was separated by silica gel column chromatography developed by dichloromethane and methanol. 5-fluoro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester (210 mg) was obtained as a white solid. EI-MS: m/z 238 (MH+); 1H-NMR (CDCl3): δ 1.50 (3H, t, J=7.3 Hz), 2.82 (3H, s), 4.46 (2H, q, J=7.3 Hz), 6.99 (1H, dd, J=3.3 Hz, 8.9 Hz), 7.15 (1H, dd, J=8.9 Hz, 10.6 Hz). And 7-fluoro-4-methyl-benzofuran-2-carboxylic acid ethyl ester was obtained as a colorless oil. EI-MS: m/z 238 (MH+); 1H-NMR (CDCl3): δ 1.44 (3H, t, J=7.3 Hz), 2.76 (3H, s), 4.46 (2H, q, J=7.3 Hz), 6.47 (1H, dd, J=3.0 Hz, 8.6 Hz), 6.97 (1H, dd, J=8.6 Hz, 10.2 Hz).

Workup

  1. customThe reaction was quenched by the addition of water (10 ml)
  2. extractionextracted with ethyl acetate (20 ml)
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe mixture was separated by silica gel column chromatography

Sources & evidence

ORD record
ord-47fb3f8450ff42f89170af0bd1b57867
Source dataset
uspto-grants-2002_04
Patent number
US06376491B1

Reaction notes

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