Tetrahydrofuran → Racemic 1,3,5-Tris(1-(4-methoxyphenyl)ethyl)benzene

HRID 41718Notes

Reaction equation

HRID 41718 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:16]=[C:15]([C:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[CH2:18])[CH:14]=[C:13]([C:27]([C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH2:28])[CH:12]=2)=[CH2:10])=[CH:5][CH:4]=1.C1COCC1.[H][H]>[Pd].CCO>[CH3:36][O:35][C:32]1[CH:31]=[CH:30][C:29]([CH:27]([C:13]2[CH:14]=[C:15]([CH:17]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)[CH3:18])[CH:16]=[C:11]([CH:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH3:10])[CH:12]=2)[CH3:28])=[CH:34][CH:33]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 89785320HCID 89785320, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 89785327Racemic 1,3,5-Tris(1-(4-methoxyphenyl)ethyl)benzene

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1,3,5-tris(1-(4-methoxyphenyl)vinyl)benzene (4) (19.61 g, 41 mmol), 5% Pd/C (500 mg), THF (50 mL) and EtOH (50 mL) was hydrogenated (50 torr) on a Parr® apparatus for 5 h. After this time the uptake of hydrogen ceased. The mixture was filtered through diatomaceous earth to remove the catalyst and rotary evaporated leaving the title compound as a colorless, viscous oil. Yield: 19.6 g (100%). 1H NMR (300 MHz, CDCl3, δ, ppm): 7.06 (d, J=8.7 Hz, 6H), 6.88-6.84 (m, 3H), 6.79 (d, J=8.9 Hz, 6H), 4.0 (q, J=7.5 Hz, 3H), 3.78 (s, 9H), 1.52 (d, J=7.3 Hz, 9H). 13C NMR (75 MHz, CDCl3, δ, ppm): 157.16, 145.83, 145.78, 145.74, 138.03, 137.99, 137.97, 127.55, 123.54, 123.46, 123.41, 113.36, 54.61, 42.94, 42.92, 21.29. Anal. calcd for C33H36O3: C, 82.46; H, 7.55. Found: C, 82.23; H, 7.40.

Workup

  1. customfor 5 h
  2. filtrationThe mixture was filtered through diatomaceous earth
  3. customto remove the catalyst
  4. customrotary evaporated

Sources & evidence

ORD record
ord-3ff30c28256b44a5825462ec88f82480
Source dataset
uspto-grants-2013_09
Patent number
US08530693B1

Reaction notes

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