Methanol → 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acid

HRID 510605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 510605
[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([O:16]C)=[O:15])#[N:2].[OH-].[Na+].O.CO>C1COCC1.C(OCC)(=O)C.Cl>[C:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[F:13])[O:9][CH2:8][CH2:7][CH:6]2[C:14]([OH:16])=[O:15])#[N:2]

Komponenten

8

Edukt 4

HCID 887MethanolHCID 962WaterHCID 14798Sodium HydroxideHCID 67080208Methyl 6-cyano-7-fluorochroman-4-carboxylate

Produkt 1

HCID 670802696-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylic acidAusbeute 95,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Methyl 6-cyano-7-fluoro-3,4-dihydro-2H-chromene-4-carboxylate (45 mg, 0.19 mmol) was diluted with THF (1 mL) followed the addition of NaOH (0.19 mL, 0.96 mmol), 200 μL of water and methanol. After stirring for 3 hours, the reaction was diluted with ethyl acetate and 2N HCl. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated to yield the title compound (40 mg, 95% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-5fd46140a86b458fb43e39349ad87388
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096567B2

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