Hexafluoropropylene → CH2=CH(CO)Nhch2CH2ocf2cfhcf3
Reaction equation
[F:1][C:2]([F:9])([F:8])[C:3]([F:7])=[C:4]([F:6])[F:5].[CH2:10]=[CH:11][C:12]([NH:14][CH2:15][CH2:16][OH:17])=[O:13].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH2:10]=[CH:11][C:12]([NH:14][CH2:15][CH2:16][O:17][C:4]([CH:3]([C:2]([F:9])([F:8])[F:1])[F:7])([F:6])[F:5])=[O:13]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Hexafluoropropene (15 g, 0.10 mol) was added over 30 minutes (nitrogen atmosphere) at 0° C. to a stirred mixture of CH2═CH(CO)NHCH2CH2OH (6.25 g, 0.054 mol), acetonitrile (180 mL) and powdered K2CO3 (3.5 g). After complete addition, the stirred reaction mixture was gradually brought to room temperature (˜1 h). The resultant pale yellow solution was filtered, and the filtrate was concentrated at the rotary evaporator. The crude product was concentrated further at ˜2 mm Hg for 15 min on a vacuum line to afford 8.5 g of CH2═CH(CO)NHCH2CH2OCF2CFHCF3 as a light yellow, viscous liquid. EI/DIP MS: m/e 265 for M+ (C8H9F6NO); 19F NMR (CDCl3) δ−75.7 (m, 3F), −81.0 to −83.0 (ddm, 2 F), and −212.1 (m, 1 F) ppm. 1H NMR (CDCl3) δ 6.3 (dd, 1H), 6.2 (dd, 1H), 6.19 (dd, 1H), 5.7 (dd, 1H), 4.8 (dm, 1H, JHF=42 Hz), 4.1 (t, 2H) and 3.6 (dt, 2H).
Workup
- additionAfter complete addition
- customthe stirred reaction mixture
- customwas gradually brought to room temperature
- custom(˜1 h)
- filtrationThe resultant pale yellow solution was filtered
- concentrationthe filtrate was concentrated at the rotary evaporator
- concentrationThe crude product was concentrated further at ˜2 mm Hg for 15 min on a vacuum line
Sources & evidence
- ORD record
- ord-5b4f0adc91f5484397dbc85ed3e975bb
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06800788B2
Reaction notes
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