Methanol → HCID 86753183, compound

HRID 2395397Notes

Reaction equation

HRID 2395397 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[CH:10][C:11]2[CH:20]=[CH:19][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:13][CH:12]=2)=[CH:5][C:4]=1[O:21][CH:22](C)[CH2:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[CH3:33]O>O1CCCC1.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:12]=[CH:13][C:14]([C:15]([O:17][CH3:18])=[O:16])=[CH:19][CH:20]=2)=[CH:5][C:4]=1[O:21][CH2:22][CH2:23][CH2:24][CH2:25][C:26]1([CH3:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH2:27]1

Participants

5

Reactant 2

HCID 887MethanolHCID 70069479HCID 70069479, compound

Product 1

HCID 86753183HCID 86753183, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (1.18 g, 2.74 mmol, 1.0 eq) methyl 4-[2-[4-methoxy-3-(1-methyl-4-phenylbutoxy)phenyl]ethenyl]benzoate and 0.600 g of 10% Pd/C in 30 ml methanol and 30 ml tetrahydrofuran was placed on a Parr hydrogenation apparatus and shaken under 20 psi H2 at room temperature for 1.5 hours. The reaction mixture was filtered through celite, concentrated in vacuo, and flash chromatographed on a silica gel column eluting with 20% ether-hexane to afford 1.00 g, 84%, of a clear oil. Elemental Analysis Calc'd for C28H32O4 : Calc'd: C, 77.75; H, 7.46. Found: C, 77.55; H, 7.55.

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationconcentrated in vacuo, and flash
  3. customchromatographed on a silica gel column
  4. washeluting with 20% ether-hexane
  5. customto afford 1.00 g, 84%

Sources & evidence

ORD record
ord-84a51f9930b5492880e77b9c7a3b9045
Source dataset
uspto-grants-1998_09
Patent number
US05814651

Reaction notes

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