Acetamide → 7-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

HRID 2422516ノート

反応式

HRID 2422516 の反応式
Br[CH2:2][C:3]([C:5]1[C:14]2[C:9](=[CH:10][C:11]([CH3:15])=[CH:12][CH:13]=2)[O:8][C:7](=[O:16])[CH:6]=1)=O.[C:17]([NH2:20])(=[O:19])[CH3:18].C(OCC)(=O)C>CN(C)C=O>[CH3:15][C:11]1[CH:10]=[C:9]2[C:14]([C:5]([C:3]3[N:20]=[C:17]([CH3:18])[O:19][CH:2]=3)=[CH:6][C:7](=[O:16])[O:8]2)=[CH:13][CH:12]=1

参加物

5

反応物 3

HCID 178AcetamideHCID 8857Ethyl AcetateHCID 866219744-(bromoacetyl)-7-methyl-2H-chromen-2-one

生成物 1

HCID 866219757-methyl-4-(2-methyl-1,3-oxazol-4-yl)-2H-chromen-2-one

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

To a solution of 4-(bromoacetyl)-7-methyl-2H-chromen-2-one (750 mg, 2.67 mmol) in N,N-dimethylformamide (2.5 mL), acetamide (158 mg, 2.67 mmol) was added. The reaction was then stirred overnight at 100° C. After cooling, the reaction mixture was dissolved with ethyl acetate and washed with water and brine, dried over MgSO4, filtered and concentrated. The crude residue obtained was pre-adsorbed on silica gel and purified by column chromatography (EtOAc/hexanes, 30:70 to 80:20) to afford the title compound. 1H NMR (400 MHz, acetone-d6): 8.52 (s, 1H), 8.21 (d, 1H), 7.23 (s, 1H), 7.21 (d, 1H), 6.52 (s, 1H), 2.57 (s, 3H), 2.49 (s, 3H).

後処理

  1. temperatureAfter cooling
  2. washwashed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue obtained
  7. custompurified by column chromatography (EtOAc/hexanes, 30:70 to 80:20)

出典と根拠

ORDレコード
ord-bde0578f06204f3ea4e1fc509bb4d86f
出典データセット
uspto-grants-2011_06
特許番号
US07960409B2

反応ノート

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