Formic Acid → Ethyl 7-(Formylamino)chroman-2-carboxylate

HRID 49464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 49464
[CH:1](O)=[O:2].C(OC(=O)C)(=O)C.[NH2:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19]2)=[CH:14][CH:13]=1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>C1COCC1>[CH:1]([NH:11][C:12]1[CH:21]=[C:20]2[C:15]([CH2:16][CH2:17][CH:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[O:19]2)=[CH:14][CH:13]=1)=[O:2]

Komponenten

7

Edukt 5

HCID 284Formic AcidHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 10632774Ethyl 7-Amino-2-chromancarboxylate

Produkt 1

HCID 20637412Ethyl 7-(Formylamino)chroman-2-carboxylateAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Mixed anhydride is prepared by stirring 1.25 equivalents of formic acid and 1 equivalent of acetic anhydride at 60° C. for 2 h. A solution of ethyl 7-amino-2-chromancarboxylate (1.25 g; 5.6 mmol) in THF is treated with triethylamine (0.78 mL; 5.6 mmol) and the previously prepared mixed anhydride (1.6 mL), stirred at ambient temperature for 1 h, poured into a saturated aqueous solution of sodium bicarbonate and extracted with ethyl ether. The combined extracts are washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound as a straw colored oil (1.4 g; 100%), identified by NMR spectral analysis.

Aufarbeitung

  1. customis prepared
  2. customthe previously prepared
  3. extractionextracted with ethyl ether
  4. washThe combined extracts are washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8e07ca4e470c49a8820efd6faab7f6d4
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06706757B2

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