Hydrochloric Acid → (3-Ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester

HRID 238648Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 238648
[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([CH2:15][CH3:16])=[C:13]([O:17]C(=O)C)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1.C[O-].[Na+].Cl>CO>[CH3:1][O:2][C:3](=[O:22])[CH2:4][C:5]1[C:14]([CH2:15][CH3:16])=[C:13]([OH:17])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:21])[CH:11]=2)[CH:6]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 59326550(4-Acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)acetic acid methyl ester

Produkt 1

HCID 59326490(3-Ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl esterAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of (4-acetoxy-3-ethyl-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (50 mg, 0.164 mmol), sodium methoxide (13 mg, 0.247 mmol), and methanol (4 mL) was stirred at room temperature for 2 hours. After the reaction mixture was acidified with concentrated hydrochloric acid to pH 5, a precipitate formed, which was then collected by filtration, and dissolved in ethyl acetate (20 mL). The organic solution was dried over sodium sulfate, and concentrated in vacuo to afford the crude product of (3-ethyl-6-fluoro-4-hydroxy-naphthalen-2-yl)-acetic acid methyl ester (42 mg, 97.7%) as a light yellow solid.

Aufarbeitung

  1. customa precipitate formed
  2. filtrationwhich was then collected by filtration
  3. dissolutiondissolved in ethyl acetate (20 mL)
  4. dry with materialThe organic solution was dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-68472c4992bc455aa287b92fbbf72277
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642629B2

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