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

HRID 1893683Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1893683
[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-b28046d5acea4e99853b9e7b52568a6f
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08513186B2

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