2-(Benzyloxy)-3-phenyl-3'-(1-(2-methoxyphenyl)vinyl)biphenyl → HCID 58238588, compound

HRID 45472Notes

Reaction equation

HRID 45472 reaction equation
C([O:8][C:9]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[O:35][CH3:36])=[CH2:28])[CH:22]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]1([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH:27]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=4[O:35][CH3:36])[CH3:28])[CH:22]=3)[C:9]=2[OH:8])[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

5

Reactant 1

HCID 582385932-(Benzyloxy)-3-phenyl-3'-(1-(2-methoxyphenyl)vinyl)biphenyl

Product 1

HCID 58238588HCID 58238588, compoundYield 95.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 34 (1.1 g, 2.35 mmol) in methanol (15 mL) and ethyl acetate (30 mL) was treated with 20% palladium on activated carbon (50% wet, 0.05 g) and was hydrogenated at 40 psi in a Parr shaker for 3 hr. The catalyst was filtered out and washed with ethyl acetate. The filtrate was stripped and the crude product was purified by chromatography on silica (50 g) 2% ethyl acetate in hexane (3 L) to afford pure E1 (0.85 g, 95%).

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with ethyl acetate
  3. customthe crude product was purified by chromatography on silica (50 g) 2% ethyl acetate in hexane (3 L)

Sources & evidence

ORD record
ord-e40f19a957074bdda1620c69c3ae9643
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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