Methyl Ethyl Ketone → [5-(3-Fluoro-benzyloxy)-pyridin-2-yl]-methanol

HRID 433212Notes

Reaction equation

Cl.[OH:2][CH2:3][C:4]1[N:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1.[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15]Br.C(=O)([O-])[O-].[K+].[K+].CC(=O)CC>O>[F:11][C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][O:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[N:9][CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-hydroxymethyl-pyridin-3-ol hydrochloride (1:1) (6.29 g, 38.9 mmol), 3-fluorobenzyl bromide (8.1 g, 42.8 mmol), potassium carbonate (10.76 g, 77.9 mmol) and 2-butanone (200 ml) was heated to 80° C. for 5 h. After cooling, water was added, and the mixture extracted with ethyl acetate. After drying of the organic layer with MgSO4, filtration and evaporation, the residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5) to give the title compound as a brown solid (6.12 g, 67%). MS: m/e=234.3 (M+H+).

Workup

temperatureAfter cooling
extractionthe mixture extracted with ethyl acetate
dry with materialAfter drying of the organic layer with MgSO4, filtration and evaporation
customthe residue was purified by chromatography (SiO2, CH2Cl2—MeOH 95:5)

Sources & evidence

ORD record: ord-212f6b30f78c462f88c2cd380fcb40f3
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06667327B2

Reaction notes

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