Benzophenone → diphenyl(pyridin-2-yl)methanol

HRID 1713381Notes

Reaction equation

HRID 1713381 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[Li]CCCC.[C:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C1COCC1>[C:21]1([C:13]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=2)[OH:20])[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 3102BenzophenoneHCID 79732-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 223294diphenyl(pyridin-2-yl)methanolYield 95.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-bromopyridine (5 g, 0.032 mol) in dry THF (150 mL) was cooled to −70° C. To this cooled solution was added n-BuLi (2.8 M, 12.4 mL, 0.034 mol) over a period of 20 min and allowed to stir for 2 h under N2 atmosphere. A solution of benzophenone (5.8 g, 0.032 mol) in dry THF (50 mL) was added to the solution at the same temperature over a period of 30 min. The reaction mixture was warmed slowly to RT and allowed to stir another 5 h at RT. The reaction mixture was concentrated under vacuum and the residue was washed with petrolieum ether. The organic layer was filtered and the filtrate was concentrated under vacuum to give the title compound (8 g, 95%).

Workup

  1. stirringto stir another 5 h at RT
  2. concentrationThe reaction mixture was concentrated under vacuum
  3. washthe residue was washed with petrolieum ether
  4. filtrationThe organic layer was filtered
  5. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-500afbbefa2745888c1b35bc5d198a20
Source dataset
uspto-grants-2010_09
Patent number
US07795270B2

Reaction notes

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