3',4',5'-Trimethoxyacetophenone → 3-[5-(Benzo[b]thien-2-yl)-2,4-di-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one

HRID 396587Notes

Reaction equation

HRID 396587 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13](=[O:15])[CH3:14])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[OH-].[Na+].[S:18]1[C:22]([C:23]2[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=2)[CH:28]=O)=[CH:21][C:20]2[CH:35]=[CH:36][CH:37]=[CH:38][C:19]1=2>C(O)C>[S:18]1[C:22]([C:23]2[C:24]([O:33][CH3:34])=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:28]=[CH:14][C:13]([C:5]3[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=3)=[O:15])[CH:30]=2)=[CH:21][C:20]2[CH:35]=[CH:36][CH:37]=[CH:38][C:19]1=2

Participants

5

Reactant 3

HCID 143453',4',5'-TrimethoxyacetophenoneHCID 14798Sodium HydroxideHCID 161159165-Benzo[b]thiophen-2-yl-2,4-dimethoxy-benzaldehyde

Product 1

HCID 694938793-[5-(Benzo[b]thien-2-yl)-2,4-di-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-oneYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3′,4′,5′-Trimethoxyacetophenone (1.62 g, 7.7 mmol) was dissolved in ethanol (50 mL). Sodium hydroxide solution (50%, 4 mL) was added and the mixture was stirred at room temperature for 30 minutes. 5-(Benzo[b]thien-2-yl)-2,4-dimethoxybenzaldehyde (2.2 g, 7.7 mmol) from Ex-6A was added, and the mixture was stirred at room temperature overnight. The resulting yellow precipitate was filtered out, rinsed with water and dried over an oil pump to give 3.4 g (92%) of the desired 3-[5-(benzo[b]thien-2-yl)-2,4-di-methoxyphenyl]-1-(3,4,5-trimethoxyphenyl)-2-propen-1-one product as a solid, m.p. 194-196° C. 1H-NMR (300 MHz, CDCl3): 8.09 (d, 1H), 7.93 (s, 1H), 7.83 (d, 1H), 7.78 (d, 1H), 7.67 (s, 1H), 7.52 (d, 1H), 7.25-7.38 (m, 4H), 6.57 (s, 1H), 3.9-4.1 (m, 15H). Anal. Calculated for C28H26O6S: C, 68.55, H, 5.34, S, 6.53; found C: 68.48, H: 5.43, S: 6.52.

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. filtrationThe resulting yellow precipitate was filtered out
  3. washrinsed with water
  4. customdried over an oil pump

Sources & evidence

ORD record
ord-68e763ff624848af97e7e986177dadb4
Source dataset
uspto-grants-2003_08
Patent number
US06608101B1

Reaction notes

Loading…