Tetrahydrofuran → HCID 86707492, Verbindung

HRID 338982Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338982
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([OH:12])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2.[O:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.COC[C@@H](O)C>O>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([O:12][C@H:16]([CH3:17])[CH2:15][O:14][CH3:18])[CH:11]=1)[N:8]=[C:7]([CH3:13])[CH:6]=[CH:5]2

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 6993459(2S)-1-methoxypropan-2-olHCID 667815176-Fluoro-8-hydroxy-2-methylquinoline

Produkt 1

HCID 86707492HCID 86707492, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of 6-fluoro-2-methylquinolin-8-ol (0.50 g, 2.8 mmol) in tetrahydrofuran (2.4 mL, 2.8 mmol) was added triphenylphosphine (2.6 g, 9.9 mmol), diisopropyl azodicarboxylate (0.91 mg, 4.5 mmol), and (S)-1-methoxypropan-2-ol (0.33 mg, 3.7 mmol) and the resultant mixture allowed to stir at ambient temperature for 24 hours. The reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts dried over sodium sulfate, filtered and concentrated under reduced pressure. Purification by normal phase chromatography on silica gel (0-2% methanol/dichloromethane) afforded the title compound which was taken on to the subsequent step without further purification, assuming theoretical yield (0.70 g, 100%) was obtained, despite being contaminated with residual triphenylphosphine oxide.

Aufarbeitung

  1. extractionextracted with dichloromethane (2×20 mL)
  2. dry with materialThe combined organic extracts dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customPurification by normal phase chromatography on silica gel (0-2% methanol/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-6be1e0c720fe4c0aac1eb0dc5a6f9ad1
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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