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

HRID 231004

반응식

HRID 231004 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 (16.8g), 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 1.7 M 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 (8.6g).

후처리

  1. additionthe mixture is treated

출처 및 근거

ORD 기록
ord-7d3e9c20adec4602852dfb9f2df8d5ea
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04844892

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