(2-(Benzyloxy)biphenyl-3-yl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol → 3'-((2-(Benzyloxy)biphenyl-3-yl)(phenyl)methyl)-2-methoxybiphenyl

HRID 45462Notes

Reaction equation

HRID 45462 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([C:15]([C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[CH:26]=[CH:27][CH:28]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)O)=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(#N)C.[PH2](O)=O>[CH2:1]([O:8][C:9]1[C:14]([CH:15]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:23]2[CH:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[O:35][CH3:36])[CH:26]=[CH:27][CH:28]=2)=[CH:13][CH:12]=[CH:11][C:10]=1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 58238602(2-(Benzyloxy)biphenyl-3-yl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol

Product 1

HCID 582385813'-((2-(Benzyloxy)biphenyl-3-yl)(phenyl)methyl)-2-methoxybiphenylYield 69%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 4124402Phosphinic AcidSolvent

Procedure

A solution of 26 (0.85 g, 1.55 mmol) in acetonitrile (50 mL) and 50% aqueous hypophosphorous acid (21 mL) was kept at reflux for 3.5 hr. The acetonitrile was removed in vacuo, the residue was diluted with ethyl acetate (150 mL) and water (80 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 (45 g) with 2% ethyl acetate in heptane (4 L) to yield pure D2 (0.42 g, 69%).

Workup

  1. temperatureat reflux for 3.5 hr
  2. customThe acetonitrile was removed in vacuo
  3. additionthe residue was diluted with ethyl acetate (150 mL) and water (80 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 (45 g) with 2% ethyl acetate in heptane (4 L)

Sources & evidence

ORD record
ord-6b5b296a370f4011ad147b42294e8195
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

Loading…