Dimedone → HCID 44136863、化合物

HRID 1020278ノート

反応式

HRID 1020278 の反応式
[CH3:1][C:2]1([CH3:10])[CH2:9][C:7](=[O:8])[CH2:6][C:4](=O)[CH2:3]1.[C:11]1([C:17]2[S:21][C:20]([CH:22]=O)=[CH:19][CH:18]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[CH2:24]([CH2:27][C:28](=O)[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:25]C.C([O-])(=O)C.[NH4+:40]>C(O)C.C(OCC)(=O)C>[CH3:10][C:2]1([CH3:1])[CH2:3][C:4]2[NH:40][C:28]([CH2:27][CH2:24][CH3:25])=[C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH:22]([C:20]3[S:21][C:17]([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)=[CH:18][CH:19]=3)[C:6]=2[C:7](=[O:8])[CH2:9]1

参加物

7

反応物 4

HCID 31358DimedoneHCID 1770535-Phenylthiophene-2-carbaldehydeHCID 517165Ammonium AcetateHCID 559036Ethyl 3-oxoheptanoate

生成物 1

HCID 44136863HCID 44136863、化合物収率 68.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of dimedone (0.70 g, 5.0 mmole) in hot ethanol (15 ml) was added 5-phenyl-2-thiophenecarboxaldehyde (0.940 g, 5.0 mmole), ethyl propylacetoacetate (0.80 ml, 5.0 mmole) and lastly ammonium acetate (0.770 g, 10.0 mmole). The mixture was held at reflux for 48 h. No precipitate was observed. The ethanol was removed in vacuo to provide a crude viscous material which was subjected to a 100 g SiO2 flash column using 40% ethyl acetate:hexanes as eluent. The desired product (1.54 g, 68%) was obtained as a yellow amorphous solid. Rf=0.37 in 1:1 ethyl acetate hexanes. 1H NMR (400 MHz; CDCl3) d 7.5 (bd, 2H, J=7.0 Hz); 7.32-7.25 (m, 2H); 7.19 (at, 1H, J=7.4 Hz); 7.04 (d, 1H, J=7.4 Hz); 6.8 (d, 1H, J=3.5 Hz); 6.38 (bs, 1H); 5.41 (s, 1H); 4.22-3.90 (m, 2H); 2.90-2.80 (m, 1H); 2.72-2.63 (m, 1H); 2.35 (d, 1H, J=16.8 Hz); 2.25 (d, 1H, J=16.8 Hz); 2.3-2.2 (On, 2H); 1.74-1.62 (m, 2H); 1.25 (at, 3H, J=7.0 Hz); 1.07 (s, 3H); 1.02 (s, 3H); 1.01 (at, 3H, J=7.0 Hz); 1.05-0.95 (m, 2H). LC MS shows MH+ at 450; 2M+H at 899 and 2M+Na at 921.

後処理

  1. temperatureat reflux for 48 h
  2. customThe ethanol was removed in vacuo
  3. customto provide a crude viscous material which

出典と根拠

ORDレコード
ord-413fb2d6373d4677baa89c69490d54cc
出典データセット
uspto-grants-2014_05
特許番号
US08716319B2

反応ノート

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