HCID 10036812, Verbindung → HCID 19701571, Verbindung

To a solution of 2-bromo-3-(1,3-dioxolan-2-yl)pyridine (m.p. 35°-40° C.; 3.60 g) synthesized by a known method in THF (60 ml) was added, at -78° C. under argon atmosphere, a 1.6M n-butyl lithium hexane solution (10.8 ml). The mixture was stirred for 15 minutes at the same temperature, to which was then added a solution of 5-bromo-2-methoxymethoxybenzaldehyde (3.83 g) in THF (10 ml). The mixture was stirred for 15 minutes at the same temperature, then stirred for further 20 minutes while warming up to room temperature. The reaction mixture was poured into a saturated aqueous saline solution, which was subjected to extraction with ethyl acetate. The extract solution was washed with a saturated aqueous saline solution, dried (anhydrous sodium sulfate) and concentrated. The concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane) to give 2-(5-bromo-α-hydroxy-2-methoxymethoxybenzyl)-3-(1,3-dioxolan-2-yl)pyridine (4.50 g) (Compound D-2). The physical properties and spectrum data are shown in Table 13 and Table 14.

1. additionwas added, at -78° C. under argon atmosphere
2. stirringThe mixture was stirred for 15 minutes at the same temperature
3. stirringstirred for further 20 minutes
4. additionThe reaction mixture was poured into a saturated aqueous saline solution, which
5. extractionwas subjected to extraction with ethyl acetate
6. washThe extract solution was washed with a saturated aqueous saline solution
7. dry with materialdried (anhydrous sodium sulfate)
8. concentrationconcentrated
9. customThe concentrate was purified by means of a silica gel column chromatography (eluent: ethyl acetate/hexane)

ORD-Eintrag

ord-ed13cc2b88304627a106b6adcf1183a8

Quelldatensatz

uspto-grants-1998_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05716971