Methyl 4-methoxy-3,5-dimethylpicolinate → 3,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

HRID 52435Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=1)=O>C1COCC1>[OH:8][CH2:9][C:11]1[C:16]([CH3:17])=[C:15]([O:18][CH3:19])[C:14]([CH3:20])=[CH:13][N:12]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Lithium aluminum hydride (0.94 g, 25.4 mmol) was dissolved in 100 ml of absolute THF and added in a dropwise manner to a stirred solution of compound 8 (2.5 g, 12.82 mmol) in 20 ml of THF at 0° C. The mixture was stirred at 0° C. for 2 hr. Excess LiAlH4 was then destroyed with ethyl acetate. The combined organic phases were dried, filtered, and evaporated in vacuo to give compound 9 (1.1 g, 50% yield). It gave same analytic data as those of an authentic sample.

Workup

customExcess LiAlH4 was then destroyed with ethyl acetate
customThe combined organic phases were dried
filtrationfiltered
customevaporated in vacuo

Sources & evidence

ORD record: ord-a4da9fc57b8547998211fad2d1f0b5b9
Source dataset: uspto-grants-1997_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05616713

Reaction notes

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