Benzoyl chloride, 3,4,5-trimethoxy- → 6-Methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene

HRID 218863노트

반응식

HRID 218863 반응식
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1.[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[C:18](Cl)=[O:19]>ClCCCl>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[C:10]([C:18](=[O:19])[C:17]3[CH:16]=[C:15]([O:14][CH3:13])[C:23]([O:24][CH3:25])=[C:22]([O:26][CH3:27])[CH:21]=3)=[C:9]([CH3:11])[S:8][C:7]=2[CH:12]=1

참가 물질

4

반응물 2

HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 221434866-Methoxy-2-methylbenzo[b]thiophene

생성물 1

HCID 591384896-Methoxy-2-methyl-3-(3,4,5-trimethoxybenzoyl)benzo[b]thiophene수율 41%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
40 °C

실험 절차

To a mixture of 6-methoxy-2-methylbenzo[b]thiophene (0.024 g; 0.132 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.052 g; 0.225 mmol) in 1,2-dichloroethane (1 ml) SnCl4 (0.023 ml) was added. The resulting mixture was stirred for 1 h at 40° C., quenched with H2O (1 ml), diluted to 15 ml with diethyl ether, washed with 5% NaHCO3 (5 ml), brine (10 ml), dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness under reduced pressure. The residue was purified by flash column chromatography (SiO2; hexane/ethyl acetate 9:1) to give pure title compound (0.020 g; 41%) as a colourless crystals. 1H-NMR(CDCl3) 2.47 (s, 3H); 3.8 (s, 6H); 3.84 (s, 3H); 3.93 (s, 3H); 6.90 (dd, 1H, J=2.4, 8.89 Hz); 7.1 (s, 2H); 7.24 (d, 1H, J=2.4 Hz); 7.42 (d, 1H, J=8.89 Hz).

후처리

  1. additionwas added
  2. customquenched with H2O (1 ml)
  3. additiondiluted to 15 ml with diethyl ether
  4. washwashed with 5% NaHCO3 (5 ml), brine (10 ml)
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customfiltrate evaporated to dryness under reduced pressure
  8. customThe residue was purified by flash column chromatography (SiO2; hexane/ethyl acetate 9:1)

출처 및 근거

ORD 기록
ord-da497a2f5656415e924fe6be95b39c98
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08198466B2

반응 노트

불러오는 중…