Sodium Hydroxide → HCID 58852716, compound

Temperature

20 °C

117.3 ml (888 mmol) of DAST were added dropwise over the course of 30 min. to a solution, cooled to 10° C., of 105.9 g (296 mmol) of 1,1-bis(6-bromo-2-pyridyl)ethan-1-ol in 1500 ml of chloroform at such a rate that the temperature did not exceed 20° C. The reaction mixture was stirred at 20° C. for 1 h and then hydrolysed dropwise with 500 ml of ice-water (care: highly exothermic reaction) with ice cooling and subsequently with 1000 ml of aqueous 3M NaOH. The organic phase was separated off, the aqueous phase was extracted twice with 100 ml of chloroform, and the combined organic phases were washed once with 500 ml of water and dried over calcium chloride. After the desiccant had been filtered off, the brown organic phase was concentrated to 200 ml and filtered through a silica-gel column. The yellow solution obtained in this way was evaporated to dryness, and the yellow, viscous oil remaining was recrystallised from 200 ml of n-heptane, giving 78.6 g (218 mmol) of the product, corresponding to a yield of 73.7%, in the form of colourless crystal needles—purity according to 1H-NMR>99.0%.

1. customdid not exceed 20° C
2. customThe organic phase was separated off
3. extractionthe aqueous phase was extracted twice with 100 ml of chloroform
4. washthe combined organic phases were washed once with 500 ml of water
5. dry with materialdried over calcium chloride
6. filtrationAfter the desiccant had been filtered off
7. concentrationthe brown organic phase was concentrated to 200 ml
8. filtrationfiltered through a silica-gel column
9. customThe yellow solution obtained in this way
10. customwas evaporated to dryness
11. customthe yellow, viscous oil remaining was recrystallised from 200 ml of n-heptane

ORD record

ord-5c25743126c343169b067664c7bea5f3

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09029539B2