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

HRID 568909Notes

Reaction equation

HRID 568909 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][Mg]Br.CO[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[O:27][CH2:28][C:29]([CH3:32])([CH3:31])[N:30]=1>O1CCCC1>[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[O:27][CH2:28][C:29]([CH3:32])([CH3:31])[N:30]=1

Participants

4

Reactant 2

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 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-862aff3b06b844879254a8ad537c86cd
Source dataset
uspto-grants-1988_03
Patent number
US04730005

Reaction notes

Loading…