Methanol → 3-Bromo-6-methoxy-2-[(methoxymethoxy)methyl]pyridine

A solution of 3-bromo-2-hydroxymethyl-6-methoxypyridine (10.6 g, 48.6 mmol) synthesized by the method described in Organic & Biomolecular Chemistry 1 (16) 2865-2876 (2003) in methylene chloride (150 mL) was successively added dropwise with diisopropylethylamine (31.4 g, 243 mmol) and chloromethyl methyl ether (13.3 g, 165 mmol) under ice cooling. The mixture was warmed to room temperature, stirred for 16 hours, and then added with methanol (30 mL), and the mixture was stirred for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1) to obtain 3-bromo-6-methoxy-2-(methoxymethyloxy)methylpyridine (12.1 g, 95%) as pale yellow oil.

1. stirringthe mixture was stirred for 30 minutes
2. concentrationThe reaction mixture was concentrated under reduced pressure
3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=30:1→20:1)

ORDレコード

ord-d835ebd44ab74d74bb2ae0e1b1e58cad

出典データセット

uspto-grants-2010_07

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07750019B2