Tetrahydrofuran → 6-Fluoro-8-(3-methoxypropoxy)-2-methylquinoline
Reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.COCCCO.[F:45][C:46]1[CH:47]=[C:48]2[C:53](=[C:54]([OH:56])[CH:55]=1)[N:52]=[C:51]([CH3:57])[CH:50]=[CH:49]2>O>[F:45][C:46]1[CH:47]=[C:48]2[C:53](=[C:54]([O:56][CH2:23][CH2:22][CH2:21][O:20][CH3:24])[CH:55]=1)[N:52]=[C:51]([CH3:57])[CH:50]=[CH:49]2Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 50 °C
Procedure
Triphenylphosphine (0.74 g, 2.8 mmol) was dissolved in tetrahydrofuran (0.94 mL, 1.1 mmol) and diisopropyl azodicarboxylate (0.35 mL, 1.8 mmol), 3-methoxypropan-1-ol (0.14 mL, 1.5 mmol) and 6-fluoro-2-methylquinolin-8-ol (0.20 g, 1.1 mmol) were added. The vessel was sealed and the mixture was stirred at 50° C. for 12 hours. The cooled reaction mixture was diluted with water (10 mL) and extracted with dichloromethane (2×20 mL). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by normal phase chromatography on silica gel (10-50% ethyl acetate/hexanes) to provide the title compound (0.22 g, 77%).
Workup
- customThe vessel was sealed
- customThe cooled reaction mixture
- extractionextracted with dichloromethane (2×20 mL)
- dry with materialThe combined organic extracts were dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe residue was purified by normal phase chromatography on silica gel (10-50% ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-20bafb282fa74cf196de78da2b888088
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08889704B2
Reaction notes
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