Trifluoroacetic acid → 4-[4-[2-(N-dodecyl-N-ethylamino]ethoxy]phenyl]-1,1,1-trifluoro-2-butanone

HRID 1383937Notes

Reaction equation

HRID 1383937 reaction equation
[CH2:1]([N:3]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])[CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][C:15](OC)([O:20]C)[C:16]([F:19])([F:18])[F:17])=[CH:9][CH:8]=1)[CH3:2].FC(F)(F)C(O)=O.C(N(CCCC(OCC)=O)CCOC1C=CC(CCC(=O)C(F)(F)F)=CC=1)CCCCCCCCCCC>>[CH2:24]([N:3]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][C:15](=[O:20])[C:16]([F:18])([F:19])[F:17])=[CH:11][CH:12]=1)[CH2:1][CH3:2])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 18319013N-Ethyl-N-[2-[4-(3,3-dimethoxy-4,4,4-trifluoro-but-1-yl)phenoxy]ethyl]dodecylamineHCID 867571224-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester

Product 1

HCID 183190164-[4-[2-(N-dodecyl-N-ethylamino]ethoxy]phenyl]-1,1,1-trifluoro-2-butanoneYield 54%

Procedure

N-Ethyl-N-[2-[4-(3,3-dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]dodecylamine (123 mg, 0.244 mmol) was treated with trifluoroacetic acid as described in the preparation of 4-[N-dodecyl-N-[2-[4-(4,4,4-trifluoro-3-oxobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester and afforded the title compound (60 mg, 54%) as a pale yellow oil.

Sources & evidence

ORD record
ord-85e529a433b94717a712afbdcee1e1e1
Source dataset
uspto-grants-2001_07
Patent number
US06255496B1

Reaction notes

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