Dicyclohexylcarbodiimide → HCID 178447885, Verbindung

HRID 36310

Reaktionsgleichung

[CH:1](/[C@H:4]1[CH2:9][CH2:8][C@H:7]([C:10]2[CH:18]=[CH:17][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:5]1)=[CH:2]\[CH3:3].[C:19]([C:21]1[CH:26]=[CH:25][C:24](O)=[CH:23][C:22]=1[F:28])#[N:20].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH:1](/[C@H:4]1[CH2:5][CH2:6][C@H:7]([C:10]2[CH:11]=[CH:12][C:13]([C:14]([O:16][C:24]3[CH:25]=[CH:26][C:21]([C:19]#[N:20])=[C:22]([F:28])[CH:23]=3)=[O:15])=[CH:17][CH:18]=2)[CH2:8][CH2:9]1)=[CH:2]\[CH3:3]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

A suspension of 2.68 g of 4-[trans-4-(1E-propenyl)cyclohexyl]benzoic acid, 1.8 g of 4-cyano-3-fluorophenol and 187 mg of 4-(dimethylamino)pyridine in 25 ml of methylene chloride was cooled to 0° C. and treated while stirring with 3.17 g of N,N'-dicyclohexylcarbodiimide. After stirring at 0° C. for 5 minutes and at room temperature for 3 hours the suspension was filtered and the filtrate was concentrated. Chromatographic purification of the residue on 50 g of basic aluminium oxide with methylene chloride and subsequent crystallization from hexane/ethyl acetate gave 2.67 g of 4-cyano-3-fluorophenyl 4-[trans-4-(1E-propenyl)cyclohexyl]benzoate as colourless crystals; m.p. (C-N) 117.5° C., cl.p. (N--I) 233.1° C.

Aufarbeitung

additiontreated
filtrationwas filtered
concentrationthe filtrate was concentrated
customChromatographic purification of the residue on 50 g of basic aluminium oxide
customwith methylene chloride and subsequent crystallization from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag: ord-16b0ae39a91848c6bc4715836e1e5cb1
Quelldatensatz: uspto-grants-1995_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05413734

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