Water → HCID 9804485, compound

HRID 1419126Notes

Reaction equation

HRID 1419126 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]([CH:28]=[C:29]([O:33][CH3:34])[C:30]=1[O:31][CH3:32])[C:25](Cl)=[O:26].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.C(OCC)(=O)C>[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.[CH3:34][O:33][C:29]1[CH:28]=[C:24]([CH:23]=[C:22]([O:21][CH3:20])[C:30]=1[O:31][CH3:32])[C:25]([C:10]1[C:11]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][C:12]=2[S:13][C:9]=1[C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:26]

Participants

8

Reactant 4

HCID 962WaterHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 2

HCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 9804485HCID 9804485, compoundYield 125.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene 5 was prepared according to the procedure of Kost et al. To a well-stirred solution of 5 (0.500 g, 1.85 mmol) and 3,4,5-trimethoxybenzoyl chloride (0.640 g, 2.77 mmol) in CH2Cl2 (20 ml), was added AlCl3 (0.123 g, 0.925 mmol) portion-wise over a 15 minute period. After 5 hours (total reaction time), water was added, and the product was isolated initially by extraction with CH2Cl2 and subsequently by extraction with ethyl acetate (EtOAc). The organic layers were separately washed with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 60:40 EtOAc/hexane) afforded 3-(3',4',5'-trimethoxybenzoyl)-2-(4'-methoxyphenyl)-6-methoxybenzo [b]thiophene (0.537 g, 1.16 mmol, 63%) as an off-white solid. Recrystallization (hexane/ethanol) afforded a highly pure crystalline sample of the compound with mp 131°-133° C. 1H-NMR (CDCl3, 360 Mhz): δ=7.66 (d,J=8.9 Hz, 1H, ArH)7.32 (d,J=2.4 Hz, 1H, ArH), 7.31 (d,J=8.8 Hz, 2H, ArH), 7.07 (s,2H, ArH), 7.01 (dd,J=8.9,2.4 Hz, 1H, ArH), 6.75 (D,J=8.8 Hz, 2H, ArH), 3.89 (s,3H, --OCH3), 3.83 (s,3H, --OCH3), 3.74 (s,3H, --OCH3), 3.73 (s, 6H, --OCH3); 13C-NMR (CDCl3, 90 Mhz): δ=192.9, 159.9, 157.7, 152.7, 143.7, 142.6, 140.1, 133.9, 132.3, 130.3, 129.9, 126.1, 124.2, 114.9, 114.1, 107.5, 104.4, 60.8, 56.1, 55.6, 55.2 HRMS (EI) M+ calcd for C26H24O6S 464.1294. and Anal. Calcd for C 26H24O6S: C, 67.23; H, 5.21; S, 6.90. Found: C, 67.20; H, 5.26; S, 6.88.

Workup

  1. washThe organic layers were separately washed with brine
  2. dry with materialdried over MgSO4
  3. customPurification by flash chromatography (silica gel, 60:40 EtOAc/hexane)

Sources & evidence

ORD record
ord-57bab8772f6e4e1e932c5216c09beea1
Source dataset
uspto-grants-1999_03
Patent number
US05886025

Reaction notes

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