Pentafluoropropionic acid → HCID 86643203, compound

HRID 1877726Notes

Reaction equation

C[Si](C)(C)[N:3]([CH2:8][CH2:9][O:10][CH3:11])[Si](C)(C)C.[CH3:14][O:15][CH2:16][CH2:17][NH:18][C:19]([CH3:24])=[CH:20][C:21](=O)[CH3:22].FC(F)(F)C(F)(F)C(O)=O.CC(C)([O-])C.[Na+]>O1CCCC1>[CH3:11][O:10][CH2:9][CH2:8][NH:3][C:21](=[CH:20][C:19](=[N:18][CH2:17][CH2:16][O:15][CH3:14])[CH3:24])[CH3:22]

Participants

Conditions

Temperature: 150 °C

Procedure

6.56 g (0.03 moles) of N,N-Bis(trimethylsilyl)-2-methoxyethylamine were mixed with 3.14 g (0.02 moles) of 4-(2-methoxyethylamino)-3-penten-2-one. To this mixture was added 4.1 g (0.026 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. 2.5 g (0.0266 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(NCH2CHOMe)CHC(HNCH2CH2OMe)Me=3.9 g (91% of theoretical).

Workup

temperaturebecame warm
customeventually forming two immiscible layers
additionwas then added dropwise over a five minute period
temperatureThe mixture warmed
customThe solvent was then removed by vacuum distillation at room temperature
distillationthe product then vacuum distilled out of the resulting residue as a clear liquid

Sources & evidence

ORD record: ord-ae6bd8f3eb794bbbab8c8530435c4cb3
Source dataset: uspto-grants-2012_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08313807B2

Reaction notes

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