PROCESS FOR PREPARING A 5-ALKEN-1-YNE COMPOUND, (6Z)-1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND, (2E,6Z)-2,6-NONADIENAL AND (2E)-CIS-6,7-EPOXY-2-NONENAL, AND 1,1-DIALKOXY-6-NONEN-2-YNE COMPOUND
申请人:SHIN-ETSU CHEMICAL CO., LTD.
公开号:US20200048161A1
公开(公告)日:2020-02-13
The object of the present invention is to provide a process for preparing a 5-alken-1-yne compound efficiently at low costs and a process for preparing (2E,6Z)-2,6-nonadienal by making use of the aforesaid process for preparing the 5-alken-1-yne compound.
There is provided a process for preparing a 5-alken-1-yne compound of the following formula (4): Y-Z-CR
1
═CR
2
—(CH
2
)
2
—C≡CH (4) in which Y in formula (4) represents a hydrogen atom or a hydroxyl group, the process comprising at least steps of: subjecting (i) an alkenylmagnesium halide compound prepared from a haloalkene compound of the following formula (1): Y-Z-CR
1
═CR
2
—(CH
2
)
2
-X
1
(1) and (ii) an alkyne compound of the following formula (2): X
2
=C≡C—Si(R
3
)(R
4
)(R
5
) (2) to a coupling reaction to form a silane compound of the following formula (3): Y-Z-CR
1
═CR
2
—(CH
2
)
2
—C≡C—Si(R
3
)(R
4
)(R
5
) (3); and subjecting the silane compound (3) to a desilylation reaction to form the 5-alken-1-yne compound (4).
本发明的目的是提供一种以低成本高效制备5-烯-1-炔化合物的方法,以及利用上述制备5-烯-1-炔化合物的方法制备(2E,6Z)-2,6-辛二烯醛的方法。提供了一种制备以下化学式(4)的5-烯-1-炔化合物的方法:Y-Z-CR1═CR2—(CH2)2—C≡CH(4),其中化学式(4)中的Y代表氢原子或羟基,该方法包括至少以下步骤:将(i)由以下化学式(1)的卤代烯烃化合物制备的烯基镁卤化物化合物:Y-Z-CR1═CR2—(CH2)2-X1(1)和(ii)以下化学式(2)的炔烃化合物:X2=C≡C—Si(R3)(R4)(R5)(2)进行偶联反应,形成以下化学式(3)的硅烷化合物:Y-Z-CR1═CR2—(CH2)2—C≡C—Si(R3)(R4)(R5)(3);并将硅烷化合物(3)进行去硅反应,形成5-烯-1-炔化合物(4)。