2-Hexenoic acid, (2E)- → 1-(4-[(E)-hex-2-enyloxy]phenyl)-2-(2-cyanothiophen-5-yl)acetylene

HRID 2121310Notes

Reaction equation

[C:1](O)(=O)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6].[OH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][C:18]2[S:22][C:21]([C:23]#[N:24])=[CH:20][CH:19]=2)=[CH:12][CH:11]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH2:1]([O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[C:17][C:18]2[S:22][C:21]([C:23]#[N:24])=[CH:20][CH:19]=2)=[CH:14][CH:15]=1)/[CH:2]=[CH:3]/[CH2:4][CH2:5][CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of N,N-dicyclohexylcarbodiimide (0.22 g) in dichloromethane (10 cm3) is added to a solution of (E)-hex-2-enoic acid (0.10 g), 1-(4-hydroxyphenyl)-2-(2-cyanothiophen-5-yl)acetylene (0.32 g), 4-(dimethylamino)pyridine (0.04 g) in dichloromethane (20 cm3), cooled in an ice bath (0° C.) under an atmosphere of nitrogen. The reaction mixture is stirred overnight, filtered to remove precipitated material and the filtrate is evaporated down under reduced pressure. The crude product is purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C.)/ethyl acetate mixture as eluent, followed by recrystallisation from ethanol to yield 1-(4-[(E)-hex-2-enyloxy]phenyl)-2-(2-cyanothiophen-5-yl)acetylene (0.26 g).

Workup

filtrationfiltered
customto remove
customprecipitated material
customthe filtrate is evaporated down under reduced pressure
customThe crude product is purified by column chromatography on silica gel using a 9:1 petroleum ether (40-60° C.)/ethyl acetate mixture as eluent
customfollowed by recrystallisation from ethanol

Sources & evidence

ORD record: ord-cdc0b00791e445fa9c36b4ceccb5c263
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06696110B1

Reaction notes

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