Sodium borohydride → 6-Phenoxy-2-pyridinemethanol

HRID 1588873Notes

Reaction equation

HRID 1588873 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[N:4]=1)=[O:2].[BH4-].[Na+]>CO>[O:9]([C:5]1[N:4]=[C:3]([CH2:1][OH:2])[CH:8]=[CH:7][CH:6]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 129410066-Phenoxypyridine-2-carbaldehyde

Product 1

HCID 128791556-Phenoxy-2-pyridinemethanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The 6-phenoxy-2-pyridinylmethanol may be prepared by first reacting phenol with 2,6-dibromopyridine in dimethyl sulfoxide under basic conditions to give 2-bromo-6-phenoxypyridine. This compound is then reacted at -70° C. with n-butyllithium in diethyl ether and then with dimethylformamide at -30° C. to give 2-formyl-6-phenoxypyridine. This aldehyde is in turn reacted with sodium borohydride in methanol, yielding the corresponding 6-phenoxy-2-pyridinylmethanol.

Sources & evidence

ORD record
ord-1e6fa33e6de04a8b8461a8fc0cc2417f
Source dataset
uspto-grants-1993_06
Patent number
US05223536

Reaction notes

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