Tetrahydrofuran → HCID 178509749, compound

HRID 863373Notes

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+].[C:36]([C:38]1[CH:43]=[CH:42][C:41]([CH2:44][CH2:45][C@H:46]2[CH2:51][CH2:50][C@H:49]([C@H:52]3[CH2:57][CH2:56][C@H:55]([CH:58]=O)[CH2:54][CH2:53]3)[CH2:48][CH2:47]2)=[CH:40][CH:39]=1)#[N:37]>C(OCC)(=O)C>[F:2][CH2:3][CH2:4][CH:5]=[CH:58][C@H:55]1[CH2:56][CH2:57][C@H:52]([C@H:49]2[CH2:50][CH2:51][C@H:46]([CH2:45][CH2:44][C:41]3[CH:42]=[CH:43][C:38]([C:36]#[N:37])=[CH:39][CH:40]=3)[CH2:47][CH2:48]2)[CH2:53][CH2:54]1

Participants

Conditions

Temperature: -20 °C

Procedure

A mixture of (3-fluoropropyl)triphenylphosphonium bromide (15.1 g, 37.4 millimols) with THF (70 ml) was cooled down to -20° C., followed by adding t-BuOK (4.2 g, 37.4 millimols) to the mixture, stirring for one hour, dropwise adding to the mixture, a THF (100 ml) solution of trans-4-(trans-4-(2-(4-cyanophenyl)ethyl)cyclohexyl)cyclohexanecarbaldehyde (11.0 g, 34.0 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 was made 500 ml, to obtain raw 4-(2-(trans-4-(trans-4-(4-fluorobutenyl)cyclohexyl)cyclohexyl)ethyl)benzonitrile (11.3 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 2

Sources & evidence

ORD record: ord-25d75464911f438f994665cdf3ea59a7
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05720899

Reaction notes

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