Water → (2,4-dichloro-6-methylpyridin-3-yl)methanol

HRID 1860427Notes

Reaction equation

[Cl:1][C:2]1[N:12]=[C:11]([CH3:13])[CH:10]=[C:9]([Cl:14])[C:3]=1[C:4](OCC)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[C:9]([Cl:14])[CH:10]=[C:11]([CH3:13])[N:12]=1

Participants

Conditions

Temperature: -30 °C

Procedure

Ethyl 2,4-dichloro-6-methylnicotinate (9) (8.04 g, 34.3 mmol) was dissolved in THF (40 mL) and added to a stirred suspension of LAH (6.52 g, 0.170 mmol) in THF (80 mL) at −78° C. The mixture was stirred for 6 hours at this temperature and for 1 hour at −30° C. followed by cautious treatment with water (5.5 mL), 15% aqueous NaOH (5.5 mL) and water (16.5 mL) with vigorous stirring. The mixture was warmed to room temperature and filtered. The white precipitate was washed liberally with ethyl acetate. The combined organic portions were dried (MgSO4) and concentrated under vacuum to afford 6.40 g (97%) of (10) as a colorless oil which solidified on standing: LCMS (MH+, 192).

Workup

temperatureThe mixture was warmed to room temperature
filtrationfiltered
washThe white precipitate was washed liberally with ethyl acetate
dry with materialThe combined organic portions were dried (MgSO4)
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-701f1767c9b847389d09e9861e47ed4d
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531475B1

Reaction notes

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