Diethyl Ether → [3-(Hex-5-en-1-yl)oxiran-2-yl]methanol

2.72 g (19.4 mM) (E)-nona-2,8-diene-1-ol (11) is added into the reaction mixture after another 5 minutes. Then, after yet another 5 minutes, 6.9 ml of a 3.39 molar solution in toluene (23.4 mM) of tertiary butyl hydroperoxide is added. The reaction mixture is allowed to react for 3 days at -25° C. Subsequently, the reaction vessel is put into an ice bath and 10 ml (1 ml per mM tetraisopropyl titantate added) saturated aqueous sodium sulfate solution and another 100 ml diethyl ether are added to the reaction mixture. The reaction solution is vigorously agitated for approximately 1 hour until the solution has warmed up to room temperature. The gelatinous orange-colored precipitation is separated out by means of a glass filter, washed twice with 100 ml quantities of ether and dried by suction. The solvent is evaporated from the combined filtrates and the residue is mixed with 100 ml ether and 2 ml dimethyl sulfide in order to destroy excess tertiary butyl hydroperoxide. The solution is agitated for one hour. Then, 50 ml 1 molar sodium hydroxide is added and the mixture is agitated another 3-4 hours. The ether phase is separated out, washed with 2×40 ml water, dried over magnesium sulfate and, after evaporation of the solvent in a vacuum, 2.48 g (15.9 mM) 2S, 3S-2-epoxy-1-hydroxynon-8-ene (III) is obtained by bulb tube distillation at 110° C./0.5 mm pressure. This corresponds to a yield of 82%.

1. customto react for 3 days at -25° C
2. customSubsequently, the reaction vessel is put into an ice bath
3. customThe gelatinous orange-colored precipitation
4. customis separated out by means of a glass
5. filtrationfilter
6. washwashed twice with 100 ml quantities of ether
7. customdried by suction
8. customThe solvent is evaporated from the combined filtrates
9. additionthe residue is mixed with 100 ml ether and 2 ml dimethyl sulfide in order
10. customto destroy excess tertiary butyl hydroperoxide
11. stirringThe solution is agitated for one hour
12. additionThen, 50 ml 1 molar sodium hydroxide is added
13. stirringthe mixture is agitated another 3-4 hours
14. customThe ether phase is separated out
15. washwashed with 2×40 ml water
16. dry with materialdried over magnesium sulfate
17. customafter evaporation of the solvent in a vacuum, 2.48 g (15.9 mM) 2S

ORD record

ord-612c4d139b504c18a80ab8ebe33c9d34

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04772727