Triphenylphosphine → 2-(Azidomethyl)-5-(difluoromethyl)furan
Reaction equation
[F:1][CH:2]([F:10])[C:3]1[O:7][C:6]([CH2:8]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:56]=[N+:57]=[N-:58])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1.ClCCl>[N:56]([CH2:8][C:6]1[O:7][C:3]([CH:2]([F:10])[F:1])=[CH:4][CH:5]=1)=[N+:57]=[N-:58]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of (5-(difluoromethyl)furan-2-yl)methanol (0.55 g, 3.72 mmol), triphenylphosphine (1.07 g, 4.09 mmol) and diethylazodicarboxylate (0.64 mL, 4.09 mmol) in anhydrous tetrahydrofuran (20 mL) was added diphenylphosphorylazide (0.88 mL, 4.09 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (40 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/9) to afford 2-(azidomethyl)-5-(difluoromethyl)furan as a yellow oil in 77% yield (0.50 g): 1H NMR (300 MHz, CDCl3) δ 6.61 (d, J=3.3 Hz, 1H), 6.58 (t, J=54.3 Hz, 1H), 6.37 (d, J=3.3 Hz, 1H), 4.30 (s, 2H); MS (ES+) m/z 172.2 (M+1).
Workup
- washwashed with water and brine
- dry with materialThe organic solution was dried over anhydrous sodium sulphate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue was purified by column chromatography
- washeluted with ethyl acetate/hexane (1/9)
Sources & evidence
- ORD record
- ord-cff9a5fea9b342778c8633fd23e4199c
- Source dataset
- uspto-grants-2012_10
- Patent number
- US08293768B2
Reaction notes
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