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

HRID 1700417Notes

Reaction equation

HRID 1700417 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-cf8f4ddc16a14b1cb3a0730300af4791
Source dataset
uspto-grants-2002_02
Patent number
US06350777B2

Reaction notes

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