Water → 2-(3-Bromo-alpha-hydroxybenzyl)-3-methoxymethoxypyridine

To a solution of 2-bromo-3-methoxymethoxypyridine (9.11 g) in diethyl ether (200 mL) was added, at -78° C., a 1.6M n-butyl lithium hexane solution (29 mL). The mixture was stirred for one hour at the same temperature, to which was further added a solution of 3-bromobenzaldehyde (6.0 mL) in diethyl ether (5 mL), and the mixture was stirred for one hour at the same temperature. The reaction mixture was poured into water, which was subjected to extraction with ethyl acetate. The extract was washed with a saturated aqueous saline solution, which was then dried (sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column (ethyl acetate--hexane) to afford 2-(3-bromo-α-hydroxybenzyl)-3-methoxymethoxypyridine (10.89 g) (compound A-1). Physical properties and spectrum data of the product are shown in Table 1 and Table 2. In substantially the same manner as above, compounds A-2 to A-4, and A-6 to A-7 shown in Table 1 were produced.

1. stirringthe mixture was stirred for one hour at the same temperature
2. extractionwas subjected to extraction with ethyl acetate
3. washThe extract was washed with a saturated aqueous saline solution, which
4. dry with materialwas then dried (sodium sulfate)
5. concentrationconcentrated
6. customThe concentrate was purified by means of a silica gel column (ethyl acetate--hexane)

ORD record

ord-05be92695d8a431cab5559f35ba4cc47

Source dataset

uspto-grants-1999_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05891895