Triethylamine → Methyltriethylammonium 3-cyanotetrafluoropropionate

HRID 232002Notes

Reaction equation

HRID 232002 reaction equation
[C:1]([C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([O:7]C)=[O:6])#[N:2].[CH2:13]([N:15]([CH2:18][CH3:19])[CH2:16][CH3:17])[CH3:14]>CCOCC>[CH3:1][N+:15]([CH2:18][CH3:19])([CH2:16][CH3:17])[CH2:13][CH3:14].[C:1]([C:3]([F:11])([F:12])[C:4]([F:9])([F:10])[C:5]([O-:7])=[O:6])#[N:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 13328902Methyl 3-cyano-2,2,3,3-tetrafluoropropionate

Product 1

HCID 13581304Methyltriethylammonium 3-cyanotetrafluoropropionate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A homogeneous solution of 9.3 g (0.05 mole) of methyl 3-cyanotetrafluoropropionate prepared as in Example 3, and 5.1 g (0.05 mole) of triethylamine in 25 ml of ether was stirred at 25°. After 4 days, a second layer had slowly formed; no increase was observed during an additional 2 days. Removal of volatiles under full pump at 25° gave a deliquescent yellow solid, methyltriethylammonium-3-cyanotetrafluoropropionate, mp 52°-55°. IR (CDCl3): 2965 (sat'd CH), 2255 (CN), 1690 (CO2), and 1250-1100 cm-1 (CF). NMR (CDCl3): 1H 3.47 (q, JHH 7.1 Hz, 6H, CH2 --N, 3.08 (s, 3H, CH3 --N), and 1.37 ppm (t, JHH 7.1 Hz, of m, 9H, CH3); 19F -108.5 (t, JFF 8.4 Hz, 2F, CF2CN) and -119.3 ppm (t, JFF 8.4 Hz, 2F, CF2C=O with only 3% of impurities present.

Workup

  1. customa second layer had slowly formed
  2. waitno increase was observed during an additional 2 days
  3. customRemoval of volatiles under full pump at 25°

Sources & evidence

ORD record
ord-d520fbe13b6c499b8666ad01f667b6e8
Source dataset
uspto-grants-1989_07
Patent number
US04851161

Reaction notes

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