Dimedone → HCID 44136863, 화합물

HRID 1020278

반응식

HRID 1020278 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 44136863HCID 44136863, 화합물수율 68.5%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-413fb2d6373d4677baa89c69490d54cc
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08716319B2

연결된 노트

불러오는 중…