3'-(1-(2-(Benzyloxy)-3-tert-butylphenyl)vinyl)-2-methoxybiphenyl → HCID 58238604, compound

HRID 45465Notes

Reaction equation

HRID 45465 reaction equation
C([O:8][C:9]1[C:14]([C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:13][CH:12]=[CH:11][C:10]=1[C:19]([C:21]1[CH:22]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][CH3:34])[CH:24]=[CH:25][CH:26]=1)=[CH2:20])C1C=CC=CC=1>CO.C(OCC)(=O)C.[Pd]>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:19]([C:21]2[CH:22]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[O:33][CH3:34])[CH:24]=[CH:25][CH:26]=2)[CH3:20])[C:9]=1[OH:8])([CH3:16])([CH3:17])[CH3:18]

Participants

5

Reactant 1

HCID 582386063'-(1-(2-(Benzyloxy)-3-tert-butylphenyl)vinyl)-2-methoxybiphenyl

Product 1

HCID 58238604HCID 58238604, compoundYield 59.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 28 (1.3 g, 2.9 mmol) in methanol (20 mL) and ethyl acetate (30 mL) was treated with 20% palladium on activated carbon (50% wet, 0.10 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 (60 g) with 2% ethyl acetate in hexane (3 L) to afford pure D3 (0.62 g, 59%).

Workup

  1. filtrationThe catalyst was filtered out
  2. washwashed with ethyl acetate
  3. customthe crude product was purified by chromatography on silica (60 g) with 2% ethyl acetate in hexane (3 L)

Sources & evidence

ORD record
ord-5211eb238fdd4196b52fbd32ac2b84c1
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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