Water → HCID 10025025, compound

HRID 1419131Notes

Reaction equation

HRID 1419131 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.[CH2:20]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=1)[CH3:21].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[CH2:20]([O:22][C:23]1[CH:31]=[CH:30][C:26]([C:27]([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:28])=[CH:25][CH:24]=1)[CH3:21]

Participants

7

Reactant 4

HCID 962WaterHCID 1400594-Ethoxybenzoyl ChlorideHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 10025025HCID 10025025, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a well stirred solution of 2-(4'-methoxyphenyl)-6-methoxybenzo[b]thiophene (0.300 g, 1.11 mmol) and 4-ethoxybenzoyl chloride (0.555 g, 3.01 mmol) in CH2Cl2 (45 ml) was added AlCl3 (0.502 g, 3.76 mmol) portion-wise over a 15 minute period. After 45 minutes, 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 with brine and then combined and dried over MgSO4. Purification by flash chromatography (silica gel, 70:30 EtOAc/hexanes) afforded the title compound (0.389 g, 0.93 mmol, 84%) as a white solid. Recrystallization (EtOAc/hexanes) afforded a highly pure, crystalline sample with mp 124°-125° C. 1H-NMR (CDCl3, 360 MHz): δ=7.77 (d,J=8.9 Hz, 2H, ArH), 7.52 (d,J=8.9 Hz, 1H, 8.8 Hz, 2H, ArH), 7.31 (d,J =2.4 Hz, 1H, ArH), 6.95 (dd,J=8.9,2.4 Hz, 1H, ArH), 6.76 (d,J=8.8 Hz, 2H, ArH), 6.75 (d,J=8.9 Hz, 2H, ArH), 4.01 (q,J=7.0 Hz, 2H, CH2), 3.88 (s,3H, --OCH3), 3.74 (s,3H, --OCH3), 1.39 (t,J=7.0, 3H, CH3); 13C-NMR (CDCl3, 90 Mhz): δ=193.1, 163.1, 159.7, 157.6, 142.3, 140.0, 134.0, 132.3, 130.6, 130.2, 126, 124.0, 114.7, 114.0, 114.0, 104.3, 63.7, 55.6, 55.2, 14.6. HRMS (EI) M+ calcd for C25H22O4S 418.1239, found 418.1241. Anal. Calcd for C25H22O4S: C, 71.75; H, 5.30; S, 7.66. Found: C, 71.68; H, 5.30; S, 7.61.

Workup

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

Sources & evidence

ORD record
ord-73a3b7aeb41842359e2eab5375b70759
Source dataset
uspto-grants-1999_03
Patent number
US05886025

Reaction notes

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