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Water → 3-[3'(3",4",5"-Trimethoxyphenyl)propionyl]-2-(4'methoxyphenyl)-6-methoxybenzo[b]thiophene

HRID 1419133
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HRID 1419133 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[S:13][C:12]3[CH:14]=[C:15]([O:18][CH3:19])[CH:16]=[CH:17][C:11]=3[CH:10]=2)=[CH:5][CH:4]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH2:32][CH2:33][C:34](Cl)=[O:35])[CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[CH3:31][O:30][C:26]1[CH:25]=[C:24]([CH2:32][CH2:33][C:34]([C:10]2[C:11]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:12]=3[S:13][C:9]=2[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:35])[CH:23]=[C:22]([O:21][CH3:20])[C:27]=1[O:28][CH3:29]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) ChlorideHCID 146500973-(3',4',5'-Trimethoxyphenyl)propionyl chloride

생성물 1

HCID 100743963-[3'(3",4",5"-Trimethoxyphenyl)propionyl]-2-(4'methoxyphenyl)-6-methoxybenzo[b]thiophene

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
2회
HCID 8857Ethyl Acetate용매

실험 절차

To a well-stirred solution of 2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene (0.206 g, 0.762 mmol) and 3-(3',4',5'-trimethoxyphenyl)propionyl chloride (0.390 g, 1.51 mmol) in CH2Cl2 (50 mL) was added AlCl3 (0.520 g, 3.89 mmol) portion-wise over a 15 minute period. After 18 hours (total reaction time), water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with EtOAc. The organic layers were separately washed sequentially with NaHCO3 (sat) and brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 70:30 EtOAc/hexane) afforded the title compound as an off-white solid. 1H-NMR (CDCl3, 360 Mhz): δ=7.92 (d,J=8.9 Hz, 1H, ArH), 7.35 (d,J=8.7 Hz, 2H, ArH), 7.25 (m,1H, ArH), 7.04 (dd,J=8.9,2.4 Hz, 1H, ArH), 6.93 (d,J=8.7 Hz, 2H, ArH), 6.15 (s,2H, ArH) 3.88 (s,3H, --OCH3), 3.85 ((s,3H, --OCH3), 3.78 (s, 3H, --OCH3), 3.72 (s,6H, --OCH3), 3.80 (t,2H, CH2), 3.70 (t,2H, CH2).

후처리

  1. washThe organic layers were separately washed sequentially with NaHCO3 (sat) and brine
  2. dry with materialdried over MgSO4
  3. customPurification by flash chromatography (silica gel, 70:30 EtOAc/hexane)

출처 및 근거

ORD 기록
ord-d47f875e840b4cecb09064ded4d84483
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05886025

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