4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 2-[2-(12,12,12-Trifluorododecyl)phenyl]-4,4-dimethyloxazoline

HRID 2165480Notes

Reaction equation

HRID 2165480 reaction equation
C(CCSC(C1C=CC=CC=1OCCCCCCC1C=CC=CC=1)CC(O)=O)(O)=O.C(C1C=CC=CC=1/C=C/CCC(OCC)=O)CCCCCCCCCCC.[F:58][C:59]([F:74])([F:73])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][Mg]Br.CO[C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=1[C:83]1[O:84][CH2:85][C:86]([CH3:89])([CH3:88])[N:87]=1>O1CCCC1>[F:58][C:59]([F:74])([F:73])[CH2:60][CH2:61][CH2:62][CH2:63][CH2:64][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:70][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][C:78]=1[C:83]1[O:84][CH2:85][C:86]([CH3:89])([CH3:88])[N:87]=1

Participants

6

Reactant 4

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 15617433Ethyl 5-(2-Dodecylphenyl)-E-4-pentenoateHCID 198179803-(2-Carboxyethylthio)-3-[2-(6-phenylhexyloxy)phenyl]propanoic acidHCID 178506315HCID 178506315, compound

Product 1

HCID 198179782-[2-(12,12,12-Trifluorododecyl)phenyl]-4,4-dimethyloxazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the procedures of Example 1(a), (b) and (c), 12,12,12-trifluorododecylmagnesium bromide (from 29.19 mmoles of 12,12,12-trifluorododecyl bromide and 25.71 mmoles of magnesium) was reacted with 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (20.17 mmoles) in tetrahydrofuran to give 2-[2-(12,12,12-trifluorododecyl)phenyl]-4,4-dimethyloxazoline. The oxazoline (14.39 mmoles) was converted to the methiodide salt and then reduced with sodium borohydride (13.43 mmoles) to yield the desired product as an oil.

Sources & evidence

ORD record
ord-d27dcc32a39b4d8e9aba4554b7a58d3c
Source dataset
uspto-grants-1990_07
Patent number
US04939279

Reaction notes

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