3'-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)-2-methoxybiphenyl → HCID 58238570, compound

HRID 45458Notes

Reaction equation

HRID 45458 reaction equation
C([O:8][C:9]1[C:14]([C:15]([C:17]2[CH:18]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[O:29][CH3:30])[CH:20]=[CH:21][CH:22]=2)=[CH2:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:19]1[CH:20]=[CH:21][CH:22]=[C:17]([CH:15]([C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:9]=2[OH:8])[CH3:16])[CH:18]=1

Participants

5

Reactant 1

HCID 582386073'-(1-(2-(Benzyloxy)biphenyl-3-yl)vinyl)-2-methoxybiphenyl

Product 1

HCID 58238570HCID 58238570, compoundYield 82%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of impure 23 (0.5 g, 1.06 mmol) in methanol (20 mL) and ethyl acetate (40 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 (45 g) with 2% ethyl acetate in hexane (3 L) to afford pure D1 (0.33 g, 82%).

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with ethyl acetate
  3. customthe crude product was purified by chromatography on silica (45 g) with 2% ethyl acetate in hexane (3 L)

Sources & evidence

ORD record
ord-f996ca93c6554206a50895d9d4d428a3
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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