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

HRID 1860438Notes

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 (10′) (8.04 g, 34.3 mmol) was dissolved in THF (40 mL) and added to a stirred suspension of LAH (6.52 g, 170 mmol) in THF (80 mL) at −78° C. The mixture was stirred for 6 h at this temperature and 1 h at −30° C. and treated cautiously 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(11′) 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
customto afford 6.40 g (97%) of(11′) as a colorless oil which

Sources & evidence

ORD record: ord-a4c14f4ff7ee4d2aa2226e73c335586b
Source dataset: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06531475B1

Reaction notes

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