HCID 86646120, compound → HCID 86646121, compound

Ethyl 4-ethyl-3-hydroxyhept-6-enoate (3.64 g, 18.2 mmol) was dissolved in a 2 N solution of potassium hydroxide in methanol (120 mL), and the solution was stirred overnight at room temperature. From the reaction solution, the solvent was distilled off under reduced pressure. To the residue, a 1 N aqueous sodium hydroxide solution (200 mL) was then added, followed by extraction with diethyl ether. The aqueous layer was made acidic by the addition of concentrated hydrochloric acid under ice cooling, followed by extraction with diethyl ether again. The organic layer was washed with saturated saline and dried over anhydrous magnesium sulfate. Then, the solvent was distilled off under reduced pressure to obtain the compound of interest as a pale yellow oil substance (3.14 g, <100%, mixture of diastereomers).

1. distillationFrom the reaction solution, the solvent was distilled off under reduced pressure
2. additionTo the residue, a 1 N aqueous sodium hydroxide solution (200 mL) was then added
3. extractionfollowed by extraction with diethyl ether
4. additionThe aqueous layer was made acidic by the addition of concentrated hydrochloric acid under ice cooling
5. extractionfollowed by extraction with diethyl ether again
6. washThe organic layer was washed with saturated saline
7. dry with materialdried over anhydrous magnesium sulfate
8. distillationThen, the solvent was distilled off under reduced pressure
9. customto obtain the compound of interest
10. additionas a pale yellow oil substance (3.14 g, <100%, mixture of diastereomers)

ORD record

ord-ad9de9f52f09460ba00e0b98976dc1b6

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206104B2