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Dicyclohexylcarbodiimide → HCID 20076277, Verbindung

HRID 704287
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 704287
[C:1]([C:3]1([CH2:10][CH2:11][CH3:12])[CH2:8][CH2:7][CH:6]([OH:9])[CH2:5][CH2:4]1)#[N:2].O1[C:17]2([CH2:22]CC(=O)[CH2:19][CH2:18]2)OCC1.S(C[N+]#[C-])(C1C=CC(C)=CC=1)(=O)=O.[Li+].CC([N-]C(C)C)C.C(Br)CCCCCC.[BH4-].[Na+].[CH2:55]([CH:59]1[CH2:64][CH2:63][CH:62]([CH:65]2[CH2:70][CH2:69][CH:68]([C:71]([OH:73])=O)[CH2:67][CH2:66]2)[CH2:61][CH2:60]1)[CH2:56][CH2:57][CH3:58].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:1]([C:3]1([CH2:10][CH2:11][CH2:12][CH2:22][CH2:17][CH2:18][CH3:19])[CH2:4][CH2:5][CH:6]([O:9][C:71]([CH:68]2[CH2:67][CH2:66][CH:65]([CH:62]3[CH2:61][CH2:60][CH:59]([CH2:55][CH2:56][CH2:57][CH3:58])[CH2:64][CH2:63]3)[CH2:70][CH2:69]2)=[O:73])[CH2:7][CH2:8]1)#[N:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

11

Edukt 8

HCID 10868DicyclohexylcarbodiimideHCID 123691-BromoheptaneHCID 161915Tosylmethyl isocyanideHCID 5674151,4-Dioxaspiro[4.5]decan-8-oneHCID 17121624'-Butyl-1,1'-bi(cyclohexyl)-4-carboxylic acidHCID 2724682Lithium diisopropylamide
HCID 4311764
Sodium borohydride
HCID 198194314-Cyano-4-propylcyclohexanol

Produkt 1

HCID 20076277HCID 20076277, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1 g of 4-dimethylaminopyridine and 22.3 g (0.1 mole) of 4-cyano-4-propylcyclohexanol (isomer mixture) [obtainable from 1,4-dioxaspiro[4,5]decan-8-one by introduction of the nitrile group with tosylmethyl isocyanide, alkylation with LDA and n-heptyl bromide, detachment of the keto-protective group and reduction of the ketone with NaBH4 ] are added to 26.6 g (0.1 mole) of 4'-butylbicyclohexane-4-carboxylic acid in 75 ml of CH2Cl2, with stirring. A solution of 21.7 g (0.105 mole) of dicyclohexylcarbodiimide in 50 ml of CH2Cl2 is added dropwise, while controlling the temperature, and the mixture is then stirred at room temperature for a further hour. The urea precipitated is separated off and the methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution and dried. After the solvent has been evaporated off, the residue is separated into its constituents by column chromatography (silica gel/petroleum ether (30-70):ether (5:1)). 4-(4-Cyano- 4-heptylcyclohexyloxycarbonyl)-4'-butylbicyclohexane is obtained.

Aufarbeitung

  1. stirringthe mixture is then stirred at room temperature for a further hour
  2. customThe urea precipitated
  3. customis separated off
  4. washthe methylene chloride phase is washed with dilute HCl and saturated NaHCO3 solution
  5. customdried
  6. customAfter the solvent has been evaporated off
  7. customthe residue is separated into its constituents by column chromatography (silica gel/petroleum ether (30-70):ether (5:1))

Quellen und Nachweise

ORD-Eintrag
ord-856f72d7254447e0b20c60c1fcb71910
Quelldatensatz
uspto-grants-1991_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04985583

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