Sodium Hydroxide → HCID 14152348, compound

2 ml of a 3.4 molar solution sodium bis-(2-methoxyethoxy)-aluminum hydride (Red-AlR) (6.8 mM) are slowly added to a solution of 0.61 g (3.91 mM) 2S, 3S-2-epoxy-1-hydroxynon-8-ene (III) in 100 ml tetrahydrofuran at 0° C. in an argon gas atmosphere with agitation. After the addition, the mixture is allowed to react 3 hours at 0° C. and the reaction solution is subsequently left overnight at 25° C. After a careful addition of 5 ml 1 molar sodium hydroxide solution, the mixture is allowed to react one more hour with agitation. The organic phase is separated off and the aqueous phase is washed with 30 ml ether. The combined organic phases are washed with saturated sodium chloride solution, dried over magnesium sulfate and subsequently the solvent is evaporated in a vacuum. Bulb tube distillation at 130° C./0.5 mm pressure yields 0.54 g (3.42 mM) 1,3(S)-dihydroxynon-8-ene (IV) with a melting point of approximately 20° C. This corresponds to a yield of 89%.

1. additionAfter the addition
2. customto react 3 hours at 0° C.
3. customto react one more hour with agitation
4. customThe organic phase is separated off
5. washthe aqueous phase is washed with 30 ml ether
6. washThe combined organic phases are washed with saturated sodium chloride solution
7. dry with materialdried over magnesium sulfate
8. customsubsequently the solvent is evaporated in a vacuum
9. distillationBulb tube distillation at 130° C./0.5 mm pressure

ORD record

ord-91c8f19c715a4e8c9bebee7740ea9b48

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04772727