2-(1,3-Dioxan-2-yl)ethyltriphenylphosphonium bromide → HCID 178509799, compound

HRID 863376

Reaction equation

[Br-].[O:2]1[CH2:7][CH2:6][CH2:5][O:4][CH:3]1[CH2:8][CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC([O-])(C)C.[K+].[C:35]([C:37]1[CH:42]=[CH:41][C:40]([C@H:43]2[CH2:48][CH2:47][C@H:46]([C@H:49]3[CH2:54][CH2:53][C@H:52]([CH:55]=O)[CH2:51][CH2:50]3)[CH2:45][CH2:44]2)=[CH:39][CH:38]=1)#[N:36]>C1COCC1>[O:4]1[CH2:5][CH2:6][CH2:7][O:2][CH:3]1[CH2:8][CH:9]=[CH:55][C@H:52]1[CH2:53][CH2:54][C@H:49]([C@H:46]2[CH2:45][CH2:44][C@H:43]([C:40]3[CH:39]=[CH:38][C:37]([C:35]#[N:36])=[CH:42][CH:41]=3)[CH2:48][CH2:47]2)[CH2:50][CH2:51]1

Participants

Conditions

Temperature: -20 °C

Procedure

A mixture of (2-(1,3-dioxan-2-yl)ethyl)triphenylphosphonium bromide (25.0 g, 54.7 millimols) with THF (150 ml) was cooled down to -20° C., followed by adding t-BuOK (6.1 g, 54.7 millimols) to the mixture, stirring for 30 minutes, dropwise adding to the mixture, a THF (80 ml) solution of trans-4-(trans-4-(4-cyanophenyl)cyclohexyl)cyclohexanecarbaldehyde (14.4 g, 49.8 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 4-(trans-4-(trans-4-(3-(1,3-dioxan-2-yl)propenyl)cyclohexyl)cyclohexyl)benzonitrile (17.5 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
extractionexcept that the quantity of ethyl acetate used for extraction

Sources & evidence

ORD record: ord-a1349c1cfa6d421c9be6f9bfbae78a1e
Source dataset: uspto-grants-1998_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05720899

Linked notes

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