Diisopropylethylamine → 3-Benzyloxy-4-methoxy-2-methylpyridine

HRID 350648Notes

Reaction equation

HRID 350648 reaction equation
[CH2:1]([O:8][CH:9]1[C:14](=[O:15])[CH:13]=[CH:12][N:11]=[C:10]1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:17](N(C(C)C)CC)(C)C>CO.C(#N)C.CCCCCC>[CH2:1]([O:8][C:9]1[C:10]([CH3:16])=[N:11][CH:12]=[CH:13][C:14]=1[O:15][CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 81531DiisopropylethylamineHCID 693437942-Methyl-3-(phenylmethoxy)-4(3H)-pyridinone

Product 1

HCID 178176443-Benzyloxy-4-methoxy-2-methylpyridineYield 76%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 21959252Acetonitrile methanolSolvent

Procedure

3-Benzyloxy-2-methyl-4-pyridone (21.5 g, 0.10 mol) was suspended in methanol-acetonitrile (1:9 v/v, 400 ml). Diisopropylethylamine (18.1 g, 0.14 mol) was added to the suspension. The mixture was then stirred. A 2.0 M solution (70 ml) of tetramethylsilyldiazomethane in n-hexane was added dropwise to the mixture, and a reaction was allowed to proceed at room temperature overnight. The reaction solution was concentrated under the reduced pressure. The concentrate was applied to column chromatography on silica gel (Wako Gel C-200, n-hexane-ethyl acetate) to give 17.3 g (yield 76%) of 3-benzyloxy-4-methoxy-2-methylpyridine.

Workup

  1. concentrationThe reaction solution was concentrated under the reduced pressure

Sources & evidence

ORD record
ord-41bc8c5c6b184016b9a86e4718224b71
Source dataset
uspto-grants-2007_02
Patent number
US07183278B1

Reaction notes

Loading…