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

HRID 1626379Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1626379
[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. overnight. The reaction was cooled, then diluted with water and ethyl acetate. The layers were separated and the organic layer was dried over magnesium sulfate, filtered and concentrated to yield the title compound (465 mg, 83.9% yield).

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. customThe layers were separated
  3. dry with materialthe organic layer was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-8703ae897e8c40cebe5d31fa94c290d6
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08785445B2

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