(2-(Benzyloxy)biphenyl-3-yl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol → 3-(Phenyl(3-(pyridin-2-yl)phenyl)methyl)biphenyl-2-ol

HRID 45437

Reaction equation

HRID 45437 reaction equation
C([O:8][C:9]1[C:14]([C:15]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:18]=2)O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)C1C=CC=CC=1>C(#N)C.[PH2](O)=O>[C:29]1([CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)[CH:18]=2)[C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:9]=2[OH:8])[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 58238583(2-(Benzyloxy)biphenyl-3-yl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol

Product 1

HCID 582385943-(Phenyl(3-(pyridin-2-yl)phenyl)methyl)biphenyl-2-olYield 52%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 4124402Phosphinic AcidSolvent

Procedure

A solution of 2(0.95 g, 1.83 mmol) in acetonitrile (24 mL) and 50% aqueous hypophosphorous acid (22 mL) was kept at reflux for 64 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (200 mL) and water (100 mL). Phases were separated. The organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL) dried over sodium sulfate and filtered. The solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (80 g) with 10% ethyl acetate in hexane (3 L) to yield slightly impure A1 (0.28 g, total yield: 52%).

Workup

  1. temperatureat reflux for 64 hr
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with ethyl acetate (200 mL) and water (100 mL)
  4. customPhases were separated
  5. washThe organic phase was washed with saturated sodium bicarbonate (2×80 mL) and water (2×80 mL)
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customThe solvent was removed on a rotary evaporator
  9. customThe crude product was purified by chromatography on silica (80 g) with 10% ethyl acetate in hexane (3 L)

Sources & evidence

ORD record
ord-d78fb67aff7045568bb2c4aa53b4a082
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Linked notes

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