(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol → 2-tert-Butyl-6-(phenyl(3-(pyridin-2-yl)phenyl)methyl)phenol

HRID 45443Notes

Reaction equation

HRID 45443 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:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[CH:22]=1)O)C1C=CC=CC=1>C(#N)C.[PH2](O)=O>[C:15]([C:14]1[CH:13]=[CH:12][CH:11]=[C:10]([CH:19]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[CH:22]=2)[C:9]=1[OH:8])([CH3:18])([CH3:16])[CH3:17]

Participants

4

Reactant 1

HCID 58238572(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)(3-(pyridin-2-yl)phenyl)methanol

Product 1

HCID 582385852-tert-Butyl-6-(phenyl(3-(pyridin-2-yl)phenyl)methyl)phenolYield 19.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 4124402Phosphinic AcidSolvent

Procedure

A solution of 6 (1.12 g, 2.24 mmol) in acetonitrile (15 mL) and 50% aqueous hypophosphorous acid (10 mL) was kept at reflux for 3 hr. The acetonitrile was removed in vacuo, the residue was diluted with water (80 mL) and extracted with ethyl acetate (150 mL). The organic phase was washed with water (100 mL), saturated sodium bicarbonate (100 mL) and water (2×100 mL), dried over sodium sulfate and filtered. The solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (50 g) with 2% ethyl acetate in heptane (2 L) and 4% (3 L) to yield pure A3 (0.17 g).

Workup

  1. temperatureat reflux for 3 hr
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with water (80 mL)
  4. extractionextracted with ethyl acetate (150 mL)
  5. washThe organic phase was washed with water (100 mL), saturated sodium bicarbonate (100 mL) and water (2×100 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 (50 g) with 2% ethyl acetate in heptane (2 L) and 4% (3 L)

Sources & evidence

ORD record
ord-7eb15d3e4a4a431cb0b0932ef3b7f07c
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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