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

HRID 529274노트

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HRID 529274 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

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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-f0158105923d46a6b8af7e2e6597a9b0
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09346842B2

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