Phosphorus oxychloride → Diisopropyl Ether

HRID 1377480Notes

Reaction equation

HRID 1377480 reaction equation
[CH2:1]([O:8][C:9]1[C:10]2[N:11]([CH:15]=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.[C:24](=O)([O-])[OH:25].[K+]>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10]2[N:11]([C:15]([CH:24]=[O:25])=[C:16]([CH3:18])[N:17]=2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH:9]([O:8][CH:1]([CH3:2])[CH3:24])([CH3:14])[CH3:10]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516893Potassium BicarbonateHCID 139003368-(Benzyloxy)-2-methylimidazo[1,2-a]pyridine

Product 2

HCID 7914Diisopropyl EtherHCID 196985328-Benzyloxy-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4.77 g of 8-benzyloxy-2-methylimidazo[1,2-a]pyridine are stirred in a Vilsmeier mixture of 20 ml of dimethylformamide and 2.3 ml of phosphoryl chloride for 2.5 h at 60° C., and are worked up mit ice/water and potassium hydrogen carbonate in a usual manner. 8-Benzyloxy-2-methylimidazo[1,2-a]pyridine-3-carboxaldehyde of m.p. 105°-106° C. (from diisopropylether) is obtained, which is debenzylated according to Kaminski et al., J. Med. Chem. 28, 876 (1985), method H, to yield 3-formyl-8-hydroxy-2-methylimidazo[1,2-a]pyridine of m.p. 251°-252° C.

Sources & evidence

ORD record
ord-982f07a385f24bdf83e54bfb943266bd
Source dataset
uspto-grants-1997_09
Patent number
US05665730

Reaction notes

Loading…