Tetrahydrofuran → HCID 178506024, 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.C1COCC1.CC([O-])(C)C.[K+].[F:36][C:37]1[CH:38]=[C:39]([C@H:47]2[CH2:52][CH2:51][C@H:50]([C@H:53]3[CH2:58][CH2:57][C@H:56]([CH:59]=O)[CH2:55][CH2:54]3)[CH2:49][CH2:48]2)[CH:40]=[CH:41][C:42]=1[C:43]([F:46])([F:45])[F:44]>C(OCC)(=O)C>[F:2][CH2:3][CH2:4][CH:5]=[CH:57][C@H:56]1[CH2:55][CH2:54][C@H:53]([C@H:50]2[CH2:49][CH2:48][C@H:47]([C:39]3[CH:40]=[CH:41][C:42]([C:43]([F:46])([F:44])[F:45])=[C:37]([F:36])[CH:38]=3)[CH2:52][CH2:51]2)[CH2:58][CH2:59]1Participants
Conditions
- Temperature
- -20 °C
Procedure
A mixture of (3-fluoropropyl)triphenylphosphonium bromide (11.2 g, 27.8 millimols) with THF (50 ml) was cooled down to -20° C., followed by adding t-BuOK (3.1 g, 27.8 millimols) to the mixture, stirring for one hour, dropwise adding to the mixture, a THF (100 ml) solution of trans-4-(trans-4-(3-fluoro-4-trifluoromethylphenyl)cyclohexyl)cyclohexanecarbaldehyde (9.0 g, 25.3 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 2 except that the quantity of ethyl acetate used for extraction was made 400 ml, to obtain raw (trans-4-(trans-4-(4-fluorobutenyl)cyclohexyl)cyclohexyl)-3-fluoro-4-trifluoromethylbenzene (8.9 g).
Workup
- additiondropwise adding to the mixture
- customat -20° C.
- stirringlower, stirring the mixture at the same temperature for 2 hours
- extractionused for extraction
Sources & evidence
- ORD record
- ord-895708be46334f66bb7a65e5d64da052
- Source dataset
- uspto-grants-1998_02
- Patent number
- US05720899
Reaction notes
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