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

HRID 1381725ノート

反応式

HRID 1381725 の反応式
[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]

参加物

8

反応物 5

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

生成物 1

HCID 5708892ethyl (Z)-dodec-5-enoate収率 99.8%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
10 °C

実験手順

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).

後処理

  1. additionthe mixture is treated

出典と根拠

ORDレコード
ord-aeab639ffcba491084e187063bd07349
出典データセット
uspto-grants-1989_02
特許番号
US04803289

反応ノート

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