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

HRID 1381725

반응식

HRID 1381725 반응식
[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]

참가 물질

8

반응물 5

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

생성물 1

HCID 5708892ethyl (Z)-dodec-5-enoate수율 99.8%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8058Hexane용매

반응 조건

온도
10 °C

실험 절차

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).

후처리

  1. additionthe mixture is treated

출처 및 근거

ORD 기록
ord-aeab639ffcba491084e187063bd07349
출처 데이터셋
uspto-grants-1989_02
특허 번호
US04803289

연결된 노트

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