Pentafluoropropionic acid → HCID 86643204, compound

HRID 1877727Notes

Reaction equation

HRID 1877727 reaction equation
C[Si](C)(C)[N:3]([CH2:8][CH2:9][N:10]([CH3:12])[CH3:11])[Si](C)(C)C.[CH3:15][N:16]([CH2:18][CH2:19][NH:20][C:21]([CH3:26])=[CH:22][C:23](=O)[CH3:24])[CH3:17].FC(F)(F)C(F)(F)C(O)=O.CC(C)([O-])C.[Na+]>O1CCCC1>[CH3:11][N:10]([CH2:9][CH2:8][NH:3][C:23](=[CH:22][C:21](=[N:20][CH2:19][CH2:18][N:16]([CH3:15])[CH3:17])[CH3:26])[CH3:24])[CH3:12]

Participants

6

Reactant 4

HCID 62356Pentafluoropropionic acidHCID 13219600HCID 13219600, compoundHCID 23676156Sodium t-butoxideHCID 86643205HCID 86643205, compound

Product 1

HCID 86643204HCID 86643204, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.48 g (0.015 moles) of N,N-Bis(trimethylsilyl)-2-(N′,N′-dimethylamino)ethylamine were mixed with 1.7 g (0.01 moles) of 4-(2-(N,N-dimethylamino)ethylamino)-3-penten-2-one. To this mixture was added 1.64 g (0.0125 moles) of pentafluoropropionic acid dropwise over 5 minutes with rapid stirring. The mixture darkened and became warm, eventually forming two immiscible layers, and was allowed to stir for 1 hour. 0.98 g (0.0125 moles) of sodium t-butoxide dissolved in 5 ml of tetrahydrofuran was then added dropwise over a five minute period. The mixture warmed and became one liquid phase, which was yellow. The solvent was then removed by vacuum distillation at room temperature, and the product then vacuum distilled out of the resulting residue as a clear liquid by heating >150° C. Yield of MeC(NCH2CH2NMe2)CHC(HNCH2CH2NMe2)Me=2.05 g (85% of theoretical).

Workup

  1. temperaturebecame warm
  2. customeventually forming two immiscible layers
  3. additionwas then added dropwise over a five minute period
  4. temperatureThe mixture warmed
  5. customThe solvent was then removed by vacuum distillation at room temperature
  6. distillationthe product then vacuum distilled out of the resulting residue as a clear liquid
  7. temperatureby heating >150° C

Sources & evidence

ORD record
ord-a7df38bbc0cd43cc962124527f23242d
Source dataset
uspto-grants-2012_11
Patent number
US08313807B2

Reaction notes

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