Hexafluoropropylene → HCID 131724607, compound

HRID 392578Notes

Reaction equation

HRID 392578 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][C:15]([CH2:18][OH:19])([CH3:17])[CH3:16])=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:10]=[CH:11][C:12]([NH:14][C:15]([CH2:18][O:19][C:4]([CH:3]([C:2]([F:9])([F:8])[F:1])[F:7])([F:6])[F:5])([CH3:17])[CH3:16])=[O:13]

Participants

5

Reactant 3

HCID 8302HexafluoropropyleneHCID 10796Cesium carbonateHCID 15145670HCID 15145670, compound

Product 1

HCID 131724607HCID 131724607, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Hexafluoropropene (13 g, 0.086 mol) was added over 30 minutes to a stirred mixture of CH2═CH(CO)NHC(CH3)2CH2OH (5.0 g, 0.035 mol), acetonitrile (190 mL) and Cs2CO3 (1.0 g, 0.003 mol) at 15-20° C. The resultant light yellow solution was stirred for an additional 1 h, after which TLC analysis (eluting with CH2Cl2 and CH3OH; 17:1 v/v) indicated the reaction was complete. The solution was filtered, and the filtrate concentrated under reduced pressure to give CH2═CHC(O)NHC(CH3)2CH2OCF2CFHCF3 as a light brown liquid (7.5 g ). 19F NMR (CDCl3): δ−75.8 (m, 3F), −79.9 (dm, 1F), −82.8 (dm, 1F), and −212.3 (dm, 1F) ppm; 1H NMR (CDCl3): δ 6.2 (dd, 1H), 6.1 (dd, 1H), 5.6 (dd, 1H), 5.6 (brs, 1H, overlaps), 4.8 (dm, 2H, JHF=44 Hz), 4.2 (dm, 2H), 1.4 (s, 6H) ppm.

Workup

  1. washafter which TLC analysis (eluting with CH2Cl2 and CH3OH; 17:1 v/v)
  2. filtrationThe solution was filtered
  3. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-8101f5b178994feea73710e2926a59bd
Source dataset
uspto-grants-2004_10
Patent number
US06800788B2

Reaction notes

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