Sodium Hydroxide → HCID 67179716, compound

Under N2 at about −35° C., to a stirred solution of 1,4-cyclohexanedione monoethyleneacetal (2.57 g, 16.5 mmol) in THF (30 mL) was added a solution of LHMDS (20% in THF, 18 mL, 18.8 mmol) over about 1 h. After stirred for another 1 h, the resulted solution was added dropwise to the solution of 5-bromofuran-2-carbonyl chloride (3.20 g, 15.7 mmol) in THF (30 mL) at about −35° C. over about 0.5 h and then stirred without cooling for about 1 h. NaOH solution (2.51 g in 300 mL of water, 62.8 mmol) was added to the above solution, and the resultant mixture was heated under reflux for a further 0.5 h. The volatile was removed under reduced pressure and then the aqueous phase was acidified with 6N HCl to pH=5 at 0-10° C. and filtered. The collected solids were dried in vacuo and then recrystallized from ethanol to give 7-(5-bromofuran-2-carbonyl)-1,4-dioxaspiro[4.5]decan-8-one as a yellow solid (2.02 g, 36%), which was used without further purification.

1. stirringstirred
2. temperaturewithout cooling for about 1 h
3. temperatureunder reflux for a further 0.5 h
4. customThe volatile was removed under reduced pressure
5. customwas acidified with 6N HCl to pH=5 at 0-10° C.
6. filtrationfiltered
7. customThe collected solids were dried in vacuo
8. customrecrystallized from ethanol

ORD record

ord-893db065fd534d119f13565f7668d796

Source dataset

uspto-grants-2014_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08691816B2