Pyridine → 1-Ethoxylcarbonyl-cyclopropanyl chloroformate

HRID 1815721

Reaktionsgleichung

Reaktionsgleichung von HRID 1815721
C1COCC1.[CH2:6]([O:8][C:9]([C:11]1([OH:14])[CH2:13][CH2:12]1)=[O:10])[CH3:7].N1C=CC=CC=1.[C:21](Cl)([Cl:23])=[O:22]>C(Cl)Cl>[Cl:23][C:21]([O:14][C:11]1([C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH2:13][CH2:12]1)=[O:22]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 6371PhosgeneHCID 8028TetrahydrofuranHCID 2733706Ethyl 1-hydroxycyclopropane-1-carboxylate

Produkt 1

HCID 224992811-Ethoxylcarbonyl-cyclopropanyl chloroformate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Step 81) A THF solution (50 mL) of 1-hydroxy-cyclopropanecarboxylic acid ethyl ester (5 g, 38.4 mmol) and pyridine (3.3 mL, 41 mmol) was added dropwise a phosgen/toleune solution (25 mL, 47.5 mmol) at 0° C. in 5-10 min. the reaction mixture was allowed slowly warm up overnite. The solid was filtered off and the filtration was concentrated in vacuo. The residue was dissolved in hexane, refiltered, and concentrated in vacuo to afford.7.4 g (100%) the product. The product was dissolved in CH2Cl2 (100 mL) as a stack solution: 1H NMR (300 MHz, CHLOROFORM-D) □ ppm 1.25 (t, J=7.14 Hz, 3H), 1.37 (m, 2H), 1.57 (m, 2H), 4.21 (q, J=6.95 Hz, 2H); (ppm) 13.97, 15.75, 62.07, 62.13, 150.54, 168.71.

Aufarbeitung

  1. temperaturewas allowed slowly warm up overnite
  2. filtrationThe solid was filtered off
  3. filtrationthe filtration
  4. concentrationwas concentrated in vacuo
  5. dissolutionThe residue was dissolved in hexane
  6. concentrationconcentrated in vacuo
  7. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-ac99576a227a4a298ffb7013f6502943
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06878722B2

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