Water → HCID 10029217, compound

HRID 1700416Notes

Reaction equation

HRID 1700416 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:24]=[C:25]([CH:29]=[C:30]([O:35][CH2:36][CH3:37])[C:31]=1[O:32][CH2:33][CH3:34])[C:26](Cl)=[O:27])[CH3:21].[Al+3].[Cl-].[Cl-].[Cl-].O>C(Cl)Cl.CCOC(C)=O>[CH2:36]([O:35][C:30]1[CH:29]=[C:25]([CH:24]=[C:23]([O:22][CH2:20][CH3:21])[C:31]=1[O:32][CH2:33][CH3:34])[C:26]([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:27])[CH3:37]

Participants

7

Reactant 4

HCID 962WaterHCID 8509416-Methoxy-2-(4-methoxyphenyl)benzo[b]thiopheneHCID 6451240Aluminum(III) ChlorideHCID 12754774HCID 12754774, compound

Product 1

HCID 10029217HCID 10029217, compoundYield 88.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a well stirred solution of 2-(4′-methoxyphenyl)-6-methoxybenzo[b]thiophene (0.501 g, 1.85 mmol) and 3,4,5-triethoxybenzoyl chloride (1.00 g, 3.66 mmol) in CH2Cl2 (45 ml) was added AlCl3 (0.870 g, 6.52 mmol) portion-wise over a 15 minute period. After 30 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 (0.827 g, 1.63 mmol, 88%) as a pale yellow solid. Recrystallization (EtOAc/hexanes) afforded a highly pure, crystalline sample with mp 108-110° C. 1H-NMR (CDCl3, 360 Mhz): δ=7.64 (d, J=8.9 Hz, 1H, ArH), 7.32 (d, J=2.3 Hz, 1H, ArH), 7.29 (d, J=8.7 Hz, 2H, ArH), 7.02(s, 2H, ArH), 6.99 (dd, J=9.0, 2.4 Hz, 1H, ArH), 6.73 (d, J=8.7, 1H, ArH), 4.06 (q, J=7.1 Hz, 2H, CH2), 3.91 (q, J=7.0, 4H, CH2), 3.89 (s, 3H, —OCH3), 3.74 (s, 3H, —OCH3), 1.34 (t, J=7.0 Hz, 6H, CH3), 1.28 (t, J=7.1 Hz, 3H, CH3); 13C-NMR (CDCl3, 90 MHz): δ=193.2, 159.8, 157.7, 152.5, 143.6, 142.6, 140.0, 133.9, 132.3, 130.3, 130.1, 126.0, 124.2, 114.8, 114.0, 108.9, 104.4, 68.8, 64.6, 55.6, 55.2, 15.4, 14.7. HRMS (EI) M+ calcd for C29H30O6S 506.1763, found 506.1777. Anal. Calcd for C29H30O6S: C, 68.75; H, 5.97; S, 6.33. Found: C, 68.67; H, 5.97; S, 6.27.

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-a7550f98ee184937bfb6dd343fffae8f
Source dataset
uspto-grants-2002_02
Patent number
US06350777B2

Reaction notes

Loading…