Dicyclohexylcarbodiimide → HCID 86698886, Verbindung

HRID 76236Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 76236
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C:15]3([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]3)=[CH:11][C:10]=2[F:21])[CH:5]=[CH:6][C:7]=1[Cl:8].C1(N=C=NC2CCCCC2)CCCCC1.[O:37]1[CH2:39][CH:38]1[CH2:40]O>C(Cl)Cl>[O:37]1[CH2:39][CH:38]1[CH2:40][O:19][C:18]([C:15]1([C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][C:7]([Cl:8])=[C:2]([Cl:1])[CH:3]=3)=[C:10]([F:21])[CH:11]=2)[CH2:17][CH2:16]1)=[O:20]

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 11164GlycidolHCID 9996409Chf-5074

Produkt 1

HCID 86698886HCID 86698886, VerbindungAusbeute 42,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1-(3′,4′-Dichloro-2-fluorobiphenyl-4-yl)cyclopropanecarboxylic acid (2.00 g, 6.15 mmol), dicyclohexylcarbodiimide (DCC, 2.54 g, 12.30 mmol), 4-dimethyl-aminopyridine (DMAP, 0.075 g, 0.614 mmol), and oxiran-2-ylmethanol (0.490 ml, 7.38 mmol) were dissolved in dry DCM (40 mL). The reaction mixture was stirred at room temperature (r.t.) overnight, then it was filtered and the filtrate was evaporated to dryness to afford 4.4 g of crude. The crude was purified by gradient flash chromatography eluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v) to afford 1-(3′,4′-dichloro-2-fluorobiphenyl-4-yl)cyclopropane carboxylic acid oxiranylmethyl ester (1.0 g, 42.6% yield).

Aufarbeitung

  1. filtrationit was filtered
  2. customthe filtrate was evaporated to dryness
  3. customto afford 4.4 g of crude
  4. customThe crude was purified by gradient flash chromatography
  5. washeluting with petroleum ether/EtOAc (from 97/3 to 90/10 v/v)

Quellen und Nachweise

ORD-Eintrag
ord-adf76516f8b940948a53a132b73a1d44
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835494B2

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