1,3-Cyclohexadiene → HCID 10236664, compound

HRID 1836032Notes

Reaction equation

HRID 1836032 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:20]=[C:19]([OH:21])[CH:18]=[CH:17][C:16]=2[C:22]2[O:23][C:24]3[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][C:25]=3[CH:26]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1CCC=CC=1>CO.[Pd]>[OH:31][C:28]1[CH:29]=[CH:30][C:24]2[O:23][C:22]([C:16]3[C:15]([C:12]4[CH:11]=[CH:10][C:9]([OH:8])=[CH:14][CH:13]=4)=[CH:20][C:19]([OH:21])=[CH:18][CH:17]=3)=[CH:26][C:25]=2[CH:27]=1

Participants

5

Reactant 2

HCID 116051,3-CyclohexadieneHCID 10150878HCID 10150878, compound

Product 1

HCID 10236664HCID 10236664, compoundYield 47.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 104 (0.13 g, 0.32 mmol) in MeOH (10 mL) was treated with 0.2 g 10% Pd/C and cyclohexadiene (1 mL) and stirred at rt for 24 h. The reaction was filtered through a bed of Celite, concentrated and chromatographed on silica gel (1:1 EtOAc/hexanes) and the product was obtained as an oil which crystallized upon addition of CH2Cl2 to yield 48 mg of yellowish needles: Mp=238-239° C.; 1H NMR (DMSO-d6) δ 9.87 (brs, 1 H), 9.54 (brs, 1 H), 9.08 (br s, 1 H), 7.64 (d, 1 H, J=8.5 Hz), 7.21 (d, 1H, J=8.7 Hz), 7.05 (d, 2 H, J=8.4 Hz), 6.84 (dd, 1 H, J=8.5 Hz, 2.5 Hz), 6.76 (d, 2 H, J=8.5 Hz), 6.69 (dd, 2 H, J=6.6 Hz, 2.4 Hz), 6.63 (dd, 1 H, J=8.7 Hz, 2.4 Hz), 5.84 (s, 1H); MS 317 (M−H)−.

Workup

  1. filtrationThe reaction was filtered through a bed of Celite
  2. concentrationconcentrated
  3. customchromatographed on silica gel (1:1 EtOAc/hexanes)
  4. customthe product was obtained as an oil which
  5. customcrystallized upon addition of CH2Cl2

Sources & evidence

ORD record
ord-a581215d6d254d3ab70ba3d0b84980a2
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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