Benzophenone → Diphenyl(pyridin-3-yl)methanol

HRID 908540Notes

Reaction equation

HRID 908540 reaction equation
Br[C:2]1[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=1.CCCCCC.[Li]CCCC.[C:19]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1COCC1>[C:27]1([C:19]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)([C:2]2[CH:3]=[N:4][CH:5]=[CH:6][CH:7]=2)[OH:26])[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 3102BenzophenoneHCID 8058HexaneHCID 122863-BromopyridineHCID 178418339Butyllithium

Product 1

HCID 298509Diphenyl(pyridin-3-yl)methanolYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 3-bromopyridine (10 g, 0.063 mol) in dry THF (200 mL)/hexane (50 mL) was cooled to −90° C. To this cooled solution was added n-BuLi (2.2 M, 32 mL, 0.063 mol) slowly and allowed to stir for 30 min under N2 atmosphere. A solution of benzophenone (11.5 g, 0.063 mol) in dry THF (50 mL) was added to this at the same temperature over a period of 30 min. The reaction mixture was warmed slowly to RT and allowed to stir another 3 h at RT. The reaction mixture was cooled, quenched with water (200 mL) and extracted with ethyl acetate (2×100 mL). The organic layer was dried, concentrated under vacuum and the crude product was purified by column chromatography on silica gel (30% ethyl acetate in pet. ether) which gave the title compound (3.3 g).

Workup

  1. stirringto stir another 3 h at RT
  2. temperatureThe reaction mixture was cooled
  3. customquenched with water (200 mL)
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. customThe organic layer was dried
  6. concentrationconcentrated under vacuum
  7. customthe crude product was purified by column chromatography on silica gel (30% ethyl acetate in pet. ether) which

Sources & evidence

ORD record
ord-286d3f1566c7432b833b78d130bd39bb
Source dataset
uspto-grants-2011_09
Patent number
US08017620B2

Reaction notes

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