Sodium Bicarbonate → 5-Fluoromethyl-2-methoxymethoxymethylpyridine

HRID 1985657Notes

Reaction equation

O1CCN(S(F)(F)[F:8])CC1.[CH3:11][O:12][CH2:13][O:14][CH2:15][C:16]1[N:21]=[CH:20][C:19]([CH2:22]O)=[CH:18][CH:17]=1.C([O-])(O)=O.[Na+]>ClCCl>[F:8][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([CH2:15][O:14][CH2:13][O:12][CH3:11])=[N:21][CH:20]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 70% HF-pyridine complex (0.3 ml) is added to a solution of morpholinosulfur trifluoride (2 ml, 1.63×10−2 mol) in dichloromethane (32 ml) cooled to −78° C. and maintained under an inert atmosphere, followed by dropwise addition of 1 g (5.4 mmol) of compound (3) as a solution in CH2Cl2 (10 ml). The mixture is stirred for 2 hours at −78° C. and then poured into saturated NaHCO3 solution (75 ml). The aqueous phase is extracted with dichloromethane and the combined organic phases are washed with brine, dried over Na2SO4, filtered and concentrated under vacuum. The residue is bulb-to-bulb distilled (P: 4.7×10−2 mb, b.p.: 110-130° C.). The title compound is isolated in the form of a colorless oil (0.3 g), which is used directly in the following step.

Workup

temperaturemaintained under an inert atmosphere
extractionThe aqueous phase is extracted with dichloromethane
washthe combined organic phases are washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under vacuum
distillationdistilled (P: 4.7×10−2 mb, b.p.: 110-130° C.)

Sources & evidence

ORD record: ord-328505ba22d441858fe268eb962da443
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07547700B2

Reaction notes

Loading…