Triphenylphosphine → ethyl (Z)-dodec-5-enoate
Reaction equation
[Br-].[CH2:2]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].BrCCCCCCC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Li])CCC.O=[CH:61][CH2:62][CH2:63][CH2:64][C:65]([O:67][CH2:68][CH3:69])=[O:66]>CCOCC.CCCCCC>[C:65]([O:67][CH2:68][CH3:69])(=[O:66])[CH2:64][CH2:63][CH2:62]/[CH:61]=[CH:2]\[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
8
Reactant 5
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 10 °C
Procedure
Heptyltriphenylphosphonium bromide (16.8 g), prepared from 1-bromoheptane and triphenylphosphine analogously to undecyltriphenylphosphonium bromide as described in Example 2(2), is suspended in dry ether (300 ml) and the mixture is treated whilst stirring under nitrogen with 1.7M butyllithium in hexane (36 ml) from a syringe. The resulting bright red solution is cooled to 10° C. and treated dropwise with ethyl 5-oxopentanoate [5.5 g, prepared as described in Example 2 (1B)] in dry ether (37.5 ml). After 10 minutes, the reaction mixture is worked up by the procedure described in Example 2(2) to give ethyl (Z)-dodec-5-enoate as a yellow oil (8.6 g).
Workup
- additionthe mixture is treated
Sources & evidence
- ORD record
- ord-aeab639ffcba491084e187063bd07349
- Source dataset
- uspto-grants-1989_02
- Patent number
- US04803289
Reaction notes
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