Ethyl 4-hydroxy-3-methyl-1-benzofuran-2-carboxylate → 5-Fluoro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester

HRID 843178노트

반응식

HRID 843178 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 540733565-Fluoro-4-hydroxy-3-methyl-benzofuran-2-carboxylic acid ethyl ester수율 27.7%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-47fb3f8450ff42f89170af0bd1b57867
출처 데이터셋
uspto-grants-2002_04
특허 번호
US06376491B1

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