Triphenylphosphine → ethyl (Z)-dodec-5-enoate

HRID 1381725

Reaktionsgleichung

Reaktionsgleichung von HRID 1381725
[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]

Komponenten

8

Edukt 5

HCID 11776TriphenylphosphineHCID 123691-BromoheptaneHCID 2724567Heptyltriphenylphosphonium bromideHCID 11137279Ethyl 5-oxopentanoateHCID 178418339Butyllithium

Produkt 1

HCID 5708892ethyl (Z)-dodec-5-enoateAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittel2×HCID 8058HexaneLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

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).

Aufarbeitung

  1. additionthe mixture is treated

Quellen und Nachweise

ORD-Eintrag
ord-aeab639ffcba491084e187063bd07349
Quelldatensatz
uspto-grants-1989_02
Patentnummer
US04803289

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