Water → 7-bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran

HRID 11151ノート

反応式

HRID 11151 の反応式
[Cl:1][C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4]P(=O)(OCC)OCC.[Br:17][C:18]1[C:26]2[O:25][C:24]([CH:27]=O)=[CH:23][C:22]=2[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=1.[H-].[Na+].O>O1CCCC1>[Br:17][C:18]1[C:26]2[O:25][C:24](/[CH:27]=[CH:4]/[C:3]3[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=3[Cl:1])=[CH:23][C:22]=2[CH:21]=[C:20]([O:29][CH3:30])[CH:19]=1

参加物

6

反応物 4

HCID 962WaterHCID 24758Sodium hydrideHCID 12520073Diethyl ((2-chlorophenyl)methyl)phosphonateHCID 219804857-Bromo-5-methoxybenzofuran-2-carbaldehyde

生成物 1

HCID 219803277-bromo-2-[(E)-2-(2-chlorophenyl)ethenyl]-5-methoxy-1-benzofuran収率 84%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

To a solution of diethyl 2-chlorobenzylphosphonate (4.91 g, 0.018 mol) and 7-bromo-5-methoxybenzofuran-2-carbaldehyde (11.27 g, 0.016 mol) in tetrahydrofuran (80 mL) was added sodium hydride (60% dispersion in mineral oil, 0.74 g, 0.0185 mol). After 5 min. the reaction mixture was warmed to 60° C. for 1 h. The reaction mixture was cooled to room temperature, water (10 mL) was carefully added and the tetrahydrofuran was removed. Water (50 mL) was added and the mixture was extracted with ethyl acetate (3×100 mL). The combined ethyl acetate extracts were washed with brine (50 mL), dried over magnesium sulphate, filtered and concentrated to dryness. Trituration with diethyl ether (20 mL) gave solid material which was further washed with diethyl ether (20 ml). The liquors were concentrated and triturated with diethyl ether (10 mL), the solid being collected. The combined solids gave (859) (4.89 g, 84%). 1H NMR δ (CDCl3) 7.70 (d, J=16 Hz, 1H), 7.65 (dd, J=7.7, 1.5 Hz, 1H), 7.4 (dd, J=6.0, 1 Hz, 1H), 7.23 (m, 2H), 7.05 (d, J=2.3 Hz, 1H), 6.94 (d, J=16 Hz, 1H), 6.92 (d, J=2.3 Hz, 1H), 6.72 (s, 1H), 3.82 (s, 3H); MH+:364.9, 362.9 MH−:362.9, 360.9.

後処理

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe tetrahydrofuran was removed
  3. additionWater (50 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (3×100 mL)
  5. washThe combined ethyl acetate extracts were washed with brine (50 mL)
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customTrituration with diethyl ether (20 mL) gave solid material which
  10. washwas further washed with diethyl ether (20 ml)
  11. concentrationThe liquors were concentrated
  12. customtriturated with diethyl ether (10 mL)
  13. customthe solid being collected

出典と根拠

ORDレコード
ord-5d80c8c706d54d52b27d08212a2f23ba
出典データセット
uspto-grants-2006_08
特許番号
US07094798B1

反応ノート

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