Reaction equation
[Br-].[F:2][CH2:3][CH2:4][CH2:5][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[C:31]([C:33]1[CH:38]=[CH:37][C:36]([C@H:39]2[CH2:44][CH2:43][C@H:42]([C@H:45]3[CH2:50][CH2:49][C@H:48]([CH:51]=O)[CH2:47][CH2:46]3)[CH2:41][CH2:40]2)=[CH:35][CH:34]=1)#[N:32]>C1COCC1>[F:2][CH2:3][CH2:4]/[CH:5]=[CH:51]/[C@H:48]1[CH2:49][CH2:50][C@H:45]([C@H:42]2[CH2:43][CH2:44][C@H:39]([C:36]3[CH:37]=[CH:38][C:33]([C:31]#[N:32])=[CH:34][CH:35]=3)[CH2:40][CH2:41]2)[CH2:46][CH2:47]1Participants
5
Conditions
- Temperature
- -20 °C
Procedure
A mixture of (3-fluoropropyl)triphenylphosphonium bromide (15.0 g, 37.2 millimols) with THF (75 ml) was cooled down to -20° C., followed by adding t-BuOK (4.2 g, 37.2 millimols) to the mixture, stirring for one hour, dropwise adding to the mixture, a THF (100 ml) solution of trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexanecarbaldehyde (10.0 g, 37.2 millimols) so as to keep the temperature at -20° C. or lower, stirring the mixture at the same temperature for 2 hours, and treating the reaction product in the same manner as in Example 3, to obtain raw (E)-4-(trans-4-(trans-4-(4-fluorobutenyl)cyclohexyl)cyclohexyl)benzonitrile (9.9 g).
Workup
- additiondropwise adding to the mixture
- customat -20° C.
- stirringlower, stirring the mixture at the same temperature for 2 hours
- additiontreating the reaction product in the same manner as in Example 3
Sources & evidence
- ORD record
- ord-32e01b136d6c4f5db2631b00040d61f7
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05720899
Linked notes
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