Pyridine → Carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl ester

HRID 2405833Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2405833
[F:1][C:2]([F:9])([F:8])[C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.N1C=CC=CC=1.Cl[C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:18]>ClCCl>[F:1][C:2]([F:9])([F:8])[C:3]1([O:7][C:17](=[O:18])[O:19][C:20]2[CH:21]=[CH:22][C:23]([N+:26]([O-:28])=[O:27])=[CH:24][CH:25]=2)[CH2:6][CH2:5][CH2:4]1

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 574451561-(Trifluoromethyl)cyclobutanol

Produkt 1

HCID 57785522Carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl esterAusbeute 48,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To 1-trifluoromethyl-cyclobutanol (2.2 g, 15 mmol) in dichloromethane (7.5 mL, 2M) was added pyridine (3 mL) and 4-nitrophenyl chloroformate (4 g, 18.3 mmol). The flask was sealed and stirred at room temperature for 2 days. The reaction was diluted with dichloromethane (50 mL) and washed with 1M KHSO4(aq), saturated sodium bicarbonate, water, and brine. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by flash column chromatography (gradient elution with 10% to 40% EtOAc in hexane) gave 2.2 g (48% yield) of carbonic acid 4-nitro-phenyl ester 1-trifluoromethyl-cyclobutyl ester as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 8.35 (d, 2H), 7.50 (d, 1H), 2.78-2.85 (m, 2H), 2.58-2.70 (m, 2H), 1.9-2.1 (m, 2H).

Aufarbeitung

  1. customThe flask was sealed
  2. washwashed with 1M KHSO4(aq), saturated sodium bicarbonate, water, and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customPurification
  6. washby flash column chromatography (gradient elution with 10% to 40% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c368f40ca56c4b68a1085e8219579a98
Quelldatensatz
uspto-grants-2014_08
Patentnummer
US08809267B2

Notizen zur Reaktion

Wird geladen…