Water → Cyclooct-1-ene-1-carbaldehyde

To cyclooctanone p-toluenesulfonyl hydrazone (4.5 g) suspended in N,N,N′,N′-tetraethylenediamine (46 ml) was added dropwise at −55° C. a 1.6 M solution of n-butyllithium in hexane (38 ml). The resulting mixture was stirred at room temperature for 30 minutes under an argon atmosphere, was then cooled with ice, was mixed with DMF (5.9 ml) and was stirred at room temperature for one hour. The reaction mixture was poured into water and was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid, water and an aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate. The resulting organic layer was evaporated under reduced pressure to remove the solvent. The residue was subjected to purification using a silica gel column (ethyl acetate:hexane=1:9) to obtain cyclooctene-1-carbaldehyde (1.5 g) as a light yellow oil.

1. temperaturewas then cooled with ice
2. stirringwas stirred at room temperature for one hour
3. extractionwas extracted with ethyl acetate
4. washThe organic layer was washed with 1 N hydrochloric acid, water
5. dry with materialan aqueous saturated solution of sodium chloride, and was then dried with anhydrous magnesium sulfate
6. customThe resulting organic layer was evaporated under reduced pressure
7. customto remove the solvent
8. customThe residue was subjected to purification

ORD-Eintrag

ord-68159be375cb41eab75fbe1e71d40874

Quelldatensatz

uspto-grants-2003_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06627651B1