Ethanol → 10,11-Epoxy-3,7,10,11-tetramethyl-2,6-dodecadiene nitrile
Reaction equation
[O:1]1[C:13]([CH3:15])([CH3:14])[C:2]1([CH3:16])[CH2:3][CH2:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9](=O)[CH3:10].C(C(CC)(P(O)(O)=O)[C:20]#[N:21])C.[Na].[CH2:29](O)C>>[O:1]1[C:13]([CH3:15])([CH3:14])[C:2]1([CH3:16])[CH2:3][CH2:4][C:5]([CH3:12])=[CH:6][CH2:7][CH2:8][C:9]([CH3:29])=[CH:10][C:20]#[N:21]Participants
Procedure
To an ice cold solution containing 9.85 g. of 9,10-epoxy-6,9,10-trimethyl-undec-5-en-2-one and 7.3 g. of diethyl phosphono acetonitrile in 50 ml. of ethyl alcohol, there was added dropwise a solution containing 1.1 g. of sodium in 25 ml. of ethyl alcohol. After the addition, the reaction mixture was allowed to stand 2 hours at room temperature. After this period, the reaction mixture was dried under vacuum and poured onto ice water. After this, the reaction mixture was exhaustively extracted with diethyl ether. The combined ether extracts were washed with an aqueous saturated sodium chloride solution, dried under sodium sulfate and evaporated. By chromatography on Kieselgel with hexane-ethyl acetate (1:1 parts by volume) was obtained pure 10,11-epoxy-3,7,10,11-tetramethyl-2,6-dodecadiene nitrile, b.p. 108°-111°C./0.005 mmHg; nD20 = 1.4861.
Workup
- additioncontaining 1.1 g
- additionAfter the addition
- waitAfter this period
- customthe reaction mixture was dried under vacuum
- additionpoured onto ice water
- extractionAfter this, the reaction mixture was exhaustively extracted with diethyl ether
- washThe combined ether extracts were washed with an aqueous saturated sodium chloride solution
- customdried under sodium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-7585a177e24c4531be4495a71a58bb94
- Source dataset
- uspto-grants-1976_09
- Patent number
- US03983243
Reaction notes
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