Triethylamine → Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoate

HRID 2037353Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037353
[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:14]([CH3:15])=[CH:13][C:12]([C:16](=O)[NH2:17])=[CH:11][C:10]=1[CH3:19])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.FC(F)(F)C(OC(=O)C(F)(F)F)=O>C(Cl)Cl>[C:1]([O:5][C:6](=[O:20])[CH2:7][CH2:8][C:9]1[C:10]([CH3:19])=[CH:11][C:12]([C:16]#[N:17])=[CH:13][C:14]=1[CH3:15])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 11849882Tert-butyl 3-(2,6-dimethyl-4-carbamoylphenyl)propanoate

Produkt 1

HCID 66935544Tert-butyl 3-(4-cyano-2,6-dimethylphenyl)propanoateAusbeute 64,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To an ice-cooled solution of 3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (7.00 g, 25.2 mmol) and triethylamine (7.66 g, 75.7 mmol) in DCM (100 mL), trifluoroacetic anhydride (6.06 g, 28.8 mmol) is added slowly so that the reaction temperature stays below 15° C. The clear yellow solution is stirred at rt for 1 h before it is washed twice with water (100 mL) and concentrated. The crude product is purified by recrystallisation from methanol to give 3-(4-cyano-2,6-dimethyl-phenyl)-propionic acid tert-butyl ester (4.2 g) as a white solid, 1H NMR (CDCl3): δ 1.48 (s, 9H), 2.33-2.37 (m, 2H), 2.38 (s, 6H), 2.94-3.01 (m, 2H), 7.31 (s, 2H).

Aufarbeitung

  1. additionis added slowly so that the reaction temperature
  2. customstays below 15° C
  3. washis washed twice with water (100 mL)
  4. concentrationconcentrated
  5. customThe crude product is purified by recrystallisation from methanol

Quellen und Nachweise

ORD-Eintrag
ord-d8d1536fbfca487f8f4f724d2bf0dac6
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575200B2

Notizen zur Reaktion

Wird geladen…