Trifluoroacetic acid → 5-Cyclohexyl-2,3-bis(4-methoxyphenyl)thiophene

HRID 579738Notes

Reaction equation

HRID 579738 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]([C:22]3(O)[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]3)[S:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[CH:5][CH:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[CH:22]1([C:11]2[S:12][C:13]([C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)=[C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH:10]=2)[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 20136516HCID 20136516, compound

Product 1

HCID 201365215-Cyclohexyl-2,3-bis(4-methoxyphenyl)thiopheneYield 70.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-[4,5-bis(4-methoxyphenyl)thien-2-yl]cyclohexanol (5.8 g, 14.7 mmole) in 125 ml of methylene chloride at 0° was treated sequentially with triethylsilane (4.7 ml, 2 equiv.) and trifluoroacetic acid (1.3 ml, 1.14 equiv.). The reaction mixture was stirred for 40 minutes at 0° and for 2 hours at room temperature, and then partitioned between methylene chloride and water. The organic phase was washed with saturated aqueous sodium bicarbonate and brine, dried and concentrated in vacuo. Recrystallization from ethanol provided the title compound (3.9 g, 70%), m.p. 95°-98°. Proton NMR and infrared (IR) spectra were consistent with the assigned structure. MS: m/z 378 (M+).

Workup

  1. custompartitioned between methylene chloride and water
  2. washThe organic phase was washed with saturated aqueous sodium bicarbonate and brine
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-5f19e848f5614c108c8aec57fe324d49
Source dataset
uspto-grants-1988_06
Patent number
US04749712

Reaction notes

Loading…