Tripropylamine → HCID 57156548, compound

HRID 1248255Notes

Reaction equation

HRID 1248255 reaction equation
C(N(CCC)CCC)CC.I[CH2:12][CH2:13][C:14]([F:28])([F:27])[C:15]([F:26])([F:25])[O:16][C:17]([F:24])([F:23])[C:18]([F:22])([F:21])[C:19]#[N:20]>COCCOCCOC>[F:21][C:18]([F:22])([C:17]([F:23])([F:24])[O:16][C:15]([F:25])([F:26])[C:14]([F:27])([F:28])[CH:13]=[CH2:12])[C:19]#[N:20]

Participants

4

Reactant 2

HCID 7616TripropylamineHCID 20279170HCID 20279170, compound

Product 1

HCID 57156548HCID 57156548, compoundYield 67.1%

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Conditions

Temperature
145 °C

Procedure

In a flask fitted with a thermometer, a magnetic stirring bar, and a still head were placed 4.5 g of tri-n-propylamine, 9.1 g of 8-iodo-2,2,3,3,5,5,6,6-octafluoro-4-oxaoctanenitrile, and 6 ml of 2-methoxyethyl ether. The flask and contents were heated rapidly to 145° C. and then stirred at 130°-145° C. for 31/2 hours during which a colorless distillate was collected. Further distillate was obtained by reducing the pressure to 24 mm. The distillate was fractionally distilled to give 2,2,3,3,5,5,6,6-octafluoro-4-oxa-7-octenenitrile (4.14 g, 67.1% yield), b.p. 84° C. The 1H-NMR spectrum showed a multiple line pattern between 5.2 and 5.6 ppm; the 19F-NMR spectrum contained three lines: at -89.1 ppm for CF2 groups surrounding 0, -113.0 ppm for CF2 adjacent to CN, and -120.4 ppm for CF2 adjacent to CH=CH2 group (integral ratios 2:1:1).

Workup

  1. customIn a flask fitted with a thermometer, a magnetic stirring bar
  2. customwas collected
  3. customFurther distillate was obtained
  4. distillationThe distillate was fractionally distilled

Sources & evidence

ORD record
ord-c7cb5613ce1d488783e331c948bc1a35
Source dataset
uspto-grants-1985_06
Patent number
US04522995

Reaction notes

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