Dimethylformamide → 9-Formyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene-4-carboxylic Acid Methyl Ester

HRID 2415792Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2415792
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9](=[O:20])[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH:16][CH:17]=[O:18])[C:11]=1[OH:19].CN(C=O)C.Br[CH2:27][CH2:28][CH2:29]Cl>O.C(OCC)(=O)C>[CH3:7][O:8][C:9]([C:10]1[C:11]2[O:19][CH2:29][CH2:28][CH2:27][N:16]([CH:17]=[O:18])[C:12]=2[CH:13]=[CH:14][CH:15]=1)=[O:20]

Komponenten

7

Edukt 4

HCID 6228DimethylformamideHCID 80061-Bromo-3-chloropropaneHCID 11430Potassium Carbonate2×HCID 167564653-Formylamino-2-hydroxy-benzoic Acid Methyl Ester

Produkt 1

HCID 865900309-Formyl-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene-4-carboxylic Acid Methyl EsterAusbeute 75,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

Potassium carbonate was ground and flame dried prior to each use. 3-formylamino-2-hydroxy-benzoic acid methyl ester compound (1.952 grams, 10 mmol) and potassium carbonate (2.764 grams, 20 mmol, 2 eq.) were placed in a flask together with 100 mL of anhydrous DMF. Heated to 120° C. for 1 hour. 1-bromo-3-chloropropane (1 mL, 10 mmol, 1 eq.) was added to the reaction mixture in several portions at 120° C. and the reaction heated for an additional 3 hours. The reaction was monitored on TLC (ethyl acetate). After cooling, the reaction mixture was stripped to a minimal volume, diluted with water and extracted three times with ethyl acetate. The combined organic portions were washed with water, brine and dried over magnesium sulfate. Filtration and solvent removal afforded crude product as a thick brown syrup (1.78 grams) which was chromatographed on silica gel using 30% ethyl acetate in hexane as eluent. The product was obtained in 67% yield as light yellow solid. M+236.

Aufarbeitung

  1. temperatureflame
  2. customdried
  3. temperaturethe reaction heated for an additional 3 hours
  4. temperatureAfter cooling
  5. extractionextracted three times with ethyl acetate
  6. washThe combined organic portions were washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration and solvent removal

Quellen und Nachweise

ORD-Eintrag
ord-36f0ca6bd6b34b8bbda7772f42ca4ad5
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06821977B2

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