2-Bromopyridine → α-(4-Methoxyphenyl)-2-pyridinemethanol

HRID 1287843Notes

Reaction equation

HRID 1287843 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=1>CCOCC>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:18]([CH:19]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[OH:20])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 79732-BromopyridineHCID 312444-MethoxybenzaldehydeHCID 178418339Butyllithium

Product 1

HCID 99004α-(4-Methoxyphenyl)-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To one mole of butyl lithium (15% in hexane) at -40° C under nitrogen is added gradually a solution of 142 g (0.9 mol) of 2-bromopyridine in 340 ml. of ether, maintaining the temperature below -40° C. After stirring for 15 minutes at this temperature, a solution of 122 g (0.9 mol) of 4-methoxybenzaldehyde in 250 ml of ether is added, with the temperature below -15° C. The reaction mixture is stirred for 40 minutes at this temperature, quenched in 1.5 l ice water. The solid is filtered and washed with cold ether to give 4-methoxyphenyl-2-pyridylcarbinol, m.p. 126°-130° C.

Workup

  1. stirringThe reaction mixture is stirred for 40 minutes at this temperature
  2. customquenched in 1.5 l ice water
  3. filtrationThe solid is filtered
  4. washwashed with cold ether

Sources & evidence

ORD record
ord-b9e9eb5565e94299ab7e047b2e9a9ae7
Source dataset
uspto-grants-1976_10
Patent number
US03985887

Reaction notes

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