Acetic Acid → 7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 510717Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510717
[F:1][C:2]1[CH:11]=[C:10]2[C:5](C(O[Si](C)(C)C)(C#N)[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.[C:19]([OH:22])(=[O:21])[CH3:20]>Cl.O.C(OCC)(=O)C>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:20]([C:19]([OH:22])=[O:21])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1

Komponenten

6

Edukt 2

HCID 176Acetic AcidHCID 670801887-Fluoro-4-(trimethylsilyloxy)chroman-4-carbonitrile

Produkt 1

HCID 670802337-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acidAusbeute 83,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

7-Fluoro-4-(trimethylsilyloxy)chroman-4-carbonitrile (750 mg, 2.83 mmol) and SnCl2 dihydrate (2551 mg, 11.3 mmol) were diluted with glacial acetic acid (3 mL) and concentrated HCl (3 mL). The reaction was heated in an oil bath at 130° C. and stirred overnight. The reaction was allowed to cool, diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the title compound (465 mg, 83.9% yield).

Aufarbeitung

  1. temperatureto cool
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-d46f88be40bf49f5a230a5c557d9cddc
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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