Benzyl chloroformate → Benzyl but-3-en-1-ylcarbamate

HRID 595228Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 595228
Cl[C:2]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:3].[CH2:12]([NH2:16])[CH2:13][CH:14]=[CH2:15].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[CH2:12]([NH:16][C:2](=[O:3])[O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:13][CH:14]=[CH2:15]

Komponenten

6

Edukt 3

HCID 10387Benzyl chloroformateHCID 4437323-Buten-1-amineHCID 516892Sodium Bicarbonate

Produkt 1

HCID 14688338Benzyl but-3-en-1-ylcarbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Benzyl chloroformate (38 g, 0.22 mol) was added at 0° C. over 15 minutes to a mixture of but-3-en-1-amine (10 g, 0.14 mol) and sodium bicarbonate (35 g, 0.52 mol) in DCM (500 mL) and water (40 mL). The mixture was diluted with water and extracted with DCM. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (petroleum ether/EtOAc) to afford benzyl but-3-en-1-ylcarbamate. MS ESI calc'd. for C12H16NO2 [M+H]+ 206. found 206. 1H NMR (400 MHz, CDCl3) δ 7.36-7.30 (m, 5H), 5.80-5.70 (m, 1H), 5.11-5.01 (m, 4H), 3.79-3.25 (m, 2H), 2.29-2.24 (m, 2H).

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (petroleum ether/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5042bb1e9a8e480c97a726d774621ea3
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

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