HCID 67103776, compound → (2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)(pyridin-2-yl)methanone

HRID 45447Notes

Reaction equation

HRID 45447 reaction equation
[CH2:1]([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]1[CH:24]=[CH:23][CH:22]=[C:21]([CH:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)[OH:26])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.[O-2].[O-2].[Mn+4]>[CH2:1]([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]1[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=2)=[O:26])[CH:20]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67103776HCID 67103776, compound

Product 1

HCID 67103457(2'-(Benzyloxy)-3'-tert-butylbiphenyl-3-yl)(pyridin-2-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of crude 10 (6.1 mmol) in dichloromethane (80 mL) was treated with manganese dioxide (85%, 8 g, 15 equiv.) and this suspension was stirred at reflux for 3 hr. The solids were filtered out and washed with ethyl acetate. The solvent was removed in a rotary evaporator and the residue was purified by chromatography on silica (80 g) with 5% ethyl acetate in heptane (1 L) and 7.5% ethyl acetate in heptane (3 L) to afford pure 11 (1.64 g, 60% over 2 steps).

Workup

  1. temperatureat reflux for 3 hr
  2. filtrationThe solids were filtered out
  3. washwashed with ethyl acetate
  4. customThe solvent was removed in a rotary evaporator
  5. customthe residue was purified by chromatography on silica (80 g) with 5% ethyl acetate in heptane (1 L) and 7.5% ethyl acetate in heptane (3 L)
  6. customto afford pure 11 (1.64 g, 60% over 2 steps)

Sources & evidence

ORD record
ord-9e27c2ff18164cc0a7336c62392a2188
Source dataset
uspto-grants-2013_09
Patent number
US08541522B2

Reaction notes

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