(3-Fluoropropyl)triphenylphosphonium bromide → HCID 178444499, compound
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+].[CH2:31]([C@H:36]1[CH2:41][CH2:40][C@H:39]([C@H:42]2[CH2:47][CH2:46][C@H:45]([CH:48]=O)[CH2:44][CH2:43]2)[CH2:38][CH2:37]1)[CH2:32][CH2:33][CH2:34][CH3:35]>C1COCC1>[F:2][CH2:3][CH2:4][CH:5]=[CH:48][C@H:45]1[CH2:46][CH2:47][C@H:42]([C@H:39]2[CH2:40][CH2:41][C@H:36]([CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:37][CH2:38]2)[CH2:43][CH2:44]1Participants
5
Conditions
- Temperature
- -20 °C
Procedure
A mixture of (3-fluoropropyl)triphenylphosphonium bromide (6.9 g, 17.1 millimols) with THF (40 ml) was cooled down to -20° C., followed by adding t-BuOK (1.9 g, 17.1 millimols) to the mixture, stirring the mixture for 30 minutes, dropwise adding to the mixture, a THF (30 ml) solution of trans-4-(trans-4-pentylcyclohexyl)cyclohexanecarbaldehyde (4.1 g, 15.5 millimols) so as to keep the temperature at -20° C., stirring the mixture at the same temperature for 2 hours, and treating the reaction product in the same manner as in Example 1, except that the quantity of ethyl acetate used for extraction was made 150 ml, to obtain raw trans-(trans-4-(4-fluorobutenyl)cyclohexyl)-4-pentylcyclohexane (4.2 g).
Workup
- additiondropwise adding to the mixture
- customat -20° C.
- stirringstirring the mixture at the same temperature for 2 hours
- additiontreating the reaction product in the same manner as in Example 1
- extractionexcept that the quantity of ethyl acetate used for extraction
Sources & evidence
- ORD record
- ord-153282506a144b27a4782ff732c7f6f3
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05720899
Reaction notes
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