Methoxymethyl-triphenylphosphonium chloride → 4-Chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine

Temperature

-30 °C

(Methoxymethyl)triphenylphosphonium chloride (1.6 g, 4.7 mmol) was dissolved in THF (20 ml) and cooled to −30° C. 2.5 Molar n-BuLi in hexanes (1.89 ml, 4.7 mmol) was and the mixture stirred for 1 h. (4-chloro-3-methoxypyridin-2-yl)-(cyclopropyl)methanone (500 mg, 2.4 mmol) dissolved in THF (5 ml) was added slowly and stirred for 4 h. The reaction mixture was quenched with saturated ammonium chloride (20 mL) and stirred overnight. 25 mL ethyl acetate was added and the layers partitioned. The organic phase was dried over sodium sulfate, filtered and evaporated to dryness to obtain crude product which was purified over silica gel using 0:1 to 3:7 ethyl acetate in heptane to obtain 4-chloro-2-(1-cyclopropyl-2-methoxyvinyl)-3-methoxy-pyridine as a clear oil (361 mg, 63%).

1. additionwas added slowly
2. customThe reaction mixture was quenched with saturated ammonium chloride (20 mL)
3. stirringstirred overnight
4. addition25 mL ethyl acetate was added
5. customthe layers partitioned
6. dry with materialThe organic phase was dried over sodium sulfate
7. filtrationfiltered
8. customevaporated to dryness
9. customto obtain crude product which
10. customwas purified over silica gel using 0:1 to 3:7 ethyl acetate in heptane

ORD record

ord-82cb84e19ea948ada2694c009a7a3121

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403818B2