Triphenylphosphine → 2-Methyl-7-(oxetan-3-yl)quinoline

HRID 339077

Reaktionsgleichung

Reaktionsgleichung von HRID 339077
[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]([CH2:15][OH:16])[CH2:13]O)=[CH:7][CH:8]=2)[N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1(C)C=CC=CC=1.CN(C)C([S-])=S.[Zn+2].CN(C)C([S-])=S>[CH3:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]([CH:12]3[CH2:13][O:16][CH2:15]3)=[CH:7][CH:8]=2)[N:3]=1

Komponenten

6

Edukt 3

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 709837452-(2-Methylquinolin-7-yl)propane-1,3-diol

Produkt 1

HCID 867075512-Methyl-7-(oxetan-3-yl)quinolineAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8722ZiramKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-methylquinolin-7-yl)propane-1,3-diol (0.100 g, 0.46 mmol) and PPh3 (0.241 g, 0.921 mmol) in toluene (10 mL) was added zinc(II) dimethylcarbamodithioate (0.211 g, 0.690 mmol) and DEAD (0.145 ml, 0.921 mmol). The resulting mixture was stirred at ambient temperature for 30 hours. The solvent was removed under reduced pressure, and water (20 mL) and ethyl acetate (30 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated under reduced pressure. The residue obtained was purified by C-18 reverse phase flash chromatography (Biotage SP4 unit, C-18 25M column, 0-90% CH3CN/water gradient; 25 CV)) to give 2-methyl-7-(oxetan-3-yl)quinoline (0.020 g, 0.100 mmol, 22% yield) as a solid.

Aufarbeitung

  1. customThe solvent was removed under reduced pressure, and water (20 mL) and ethyl acetate (30 mL)
  2. additionwere added
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (sodium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue obtained
  9. customwas purified by C-18 reverse phase flash chromatography (Biotage SP4 unit

Quellen und Nachweise

ORD-Eintrag
ord-aa2505b30eb5463db44248acd9d90ade
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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