Potassium Carbonate → (4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 1261430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261430
[CH2:1]([O:8][C:9]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=[C:11]([CH2:20]Cl)[C:10]=1[CH3:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1[CH2:27][O:26][CH2:25]C1.CO.C([O-])([O-])=[O:31].[K+].[K+]>O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:25][O:26][C:27](=[O:31])[CH2:20][C:11]1[C:10]([CH3:22])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:19])[CH:17]=2)[CH:12]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 21899815MeOH tetrahydrofuranHCID 593265471-Benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene

Produkt 1

HCID 59326535(4-Benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl esterAusbeute 97,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred solution of 1-benzyloxy-3-chloromethyl-7-fluoro-2-methyl-naphthalene (18.5 g, 58.9 mmol) in a THF-methanol mixture (2:3; 500 mL) was added K2CO3 (8.94 g, 64.8 mmol) and PdCl2(PPh3)2 (2.06 g, 2.96 mmol) at room temperature. The solution was degassed by purging with argon for 5 minutes. The reaction mixture was stirred under a balloon of carbon monoxide overnight at room temperature. After this time, the reaction progress was monitored by TLC (5% ethyl acetate in hexanes). The reaction mixture was concentrated, and the obtained crude residue was diluted with water and extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated to give a crude product. Silica gel chromatography (100-200 mesh, 5% ethyl acetate-hexanes) yielded (4-benzyloxy-6-fluoro-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (5.5 g, 97.8%) as a pale yellow solid. MS cald. for C21H20FO3 [(M+H)+]: 339, obsd. 339.0.

Aufarbeitung

  1. customThe solution was degassed
  2. customby purging with argon for 5 minutes
  3. concentrationThe reaction mixture was concentrated
  4. customthe obtained crude residue
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts were washed with water and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a crude product

Quellen und Nachweise

ORD-Eintrag
ord-81a293cfcf7b48fb98d8c6c3bfc899cd
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470884B2

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