Sodium → 10,11-Epoxy-3,7,10,11-tetramethyl-2,6-dodecadienoic acid ethyl ester
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(=O)C.[CH2:17]([O:19][C:20](=[O:30])[C:21]([CH2:28][CH3:29])(CC)P(O)(O)=O)[CH3:18].[Na]>C(O)C>[CH2:17]([O:19][C:20](=[O:30])[CH:21]=[C:28]([CH3:29])[CH2:8][CH2:7][CH:6]=[C:5]([CH3:12])[CH2:4][CH2:3][C:2]1([CH3:16])[O:1][C:13]1([CH3:15])[CH3:14])[CH3:18]Participants
Procedure
To a solution of 25 g. of 9,10-epoxy-6,9,10-trimethyl-undec-5-en-2-one and 24.8 g. of diethyl phosphonoacetic acid ethyl ester in 160 ml. of absolute ethanol, there was added dropwise while cooling with ice, a solution containing 2.56 g. of sodium in 65 ml. of absolute ethyl alcohol. The mixture was allowed to stand for 14 hours at room temperature and evaporated subsequently under vacuum. The residue was poured into a standard aqueous sodium chloride solution, exhaustively extracted with diethyl ether, washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated. Fractional distillation at high vacuum gave 10,11-epoxy-3,7,10,11-tetramethyl-2,6-dodecadienoic acid ethyl ester; b.p. 110°-113°C./0.01 mmHg; nD20 = 1.4792.
Workup
- temperaturewhile cooling with ice
- additiona solution containing 2.56 g
- customevaporated subsequently under vacuum
- additionThe residue was poured into a standard aqueous sodium chloride solution
- extractionexhaustively extracted with diethyl ether
- washwashed with a saturated aqueous sodium chloride solution
- dry with materialdried over sodium sulfate
- customevaporated
- distillationFractional distillation at high vacuum
Sources & evidence
- ORD record
- ord-211de8d244c5499ea039c74bffd02fca
- Source dataset
- uspto-grants-1976_06
- Patent number
- US03962428
Reaction notes
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