Acetyl chloride → 4-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chroman

HRID 1454003ノート

反応式

HRID 1454003 の反応式
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([OH:26])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9].[C:27](Cl)(=O)C.C(=O)(O)[O-].[Na+]>CO>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]2[C:21]3[C:16](=[C:17]4[CH:24]=[CH:23][N:22]([CH3:25])[C:18]4=[CH:19][CH:20]=3)[O:15][CH:14]([O:26][CH3:27])[CH2:13]2)[CH:5]=[C:6]([O:10][CH3:11])[C:7]=1[O:8][CH3:9]

参加物

5

反応物 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 103872724-(3-Bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman

生成物 1

HCID 100028974-(3-Bromo-4,5-dimethoxyphenyl)-2-methoxy-7-methyl-pyrrolo[2,3-h]chroman収率 58%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-(3-bromo-4,5-dimethoxyphenyl)-2-hydroxy-7-methyl-pyrrolo[2,3-h]chroman (5 mg; 0.012 mmol ) in methanol (0.5 ml) at 0° C. was added acetyl chloride (10 μl). The mixture was warmed to room temperature and stirred at this temperature for 3 h. Saturated sodium bicarbonate solution was added and the reaction mixture was extracted with dichloromethane. The extract was washed with saturated sodium chloride solution, dried and evaporated. The crude product was passed through bond-elute (hexane:ethyl acetate=9:1 as eluent), giving the title compound (3 mg; 58%). 1H NMR (acetone-d6): 7.14 (d, J=2.7 Hz) and 7.13 (d, J=2.9 Hz) (1H), 6.94-7.02 (m, 2H), 6.89 and 6.88 (d each, J=8.5 Hz, 1H), 6.50-6.57 (m, 2H), 5.32 (t, J=2.6 Hz) and 5.27 (dd, J=2.3, 7.6 Hz) (1H), 4.34 (dd, J=6.6, 9.5 Hz) and 4.27 (dd, J=6.0, 11.3 Hz) (1H), 3.85, 3.82, 3.81, 3.80, 3.79, 3.78 (s each, 9H), 3.59 and 3.50 (s each, 3H), 2.43 (ddd, J=2.3, 6.6, 13.3 Hz) and 2.12-2.30 (m) (2H).

後処理

  1. extractionthe reaction mixture was extracted with dichloromethane
  2. washThe extract was washed with saturated sodium chloride solution
  3. customdried
  4. customevaporated
  5. washthrough bond-elute (hexane:ethyl acetate=9:1 as eluent)

出典と根拠

ORDレコード
ord-549057ea24964e55abfab53bb3a9c267
出典データセット
uspto-grants-2009_01
特許番号
US07476741B2

反応ノート

読み込み中…