Methyl iodide → 4,5-Dihydro-3,4,4-trimethyloxazolium iodide
Reaction equation
C1(CCCCCCCCC2C=CC=CC=2[C:21]2[O:22][CH2:23][C:24]([CH3:27])([CH3:26])[N:25]=2)C=CC=CC=1.[CH3:28][I:29]>>[I-:29].[CH3:28][N+:25]1[C:24]([CH3:27])([CH3:26])[CH2:23][O:22][CH:21]=1Participants
Procedure
Following the procedures of Example 1(a), (b) and (c), to 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). (The 8-phenyloctyl bromide was prepared from 8-phenyloctanol, carbon tetrabromide and triphenylphosphine in methylene chloride analogous to the procedure described in Example 22(a).) After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]-4,4-dimethyloxazoline as an oil. A solution of the oxazoline (11.58 mmoles) in methyl iodide (20 ml) was refluxed under argon for 18 hours. Removal of the volatiles afforded the corresponding 3,4,4-trimethyloxazolinium iodide as a white solid (mp 76.5°-78° C). To an ice cold solution of the iodide (9.46 mmoles) in methanol (35 ml) was added in portions sodium borohydride (9.20 mmoles). Treatment of the reaction mixture as in Example 1(c) results in the isolation of the desired product as an oil.
Workup
- customRemoval of the volatiles
Sources & evidence
- ORD record
- ord-0973910720434518b1bf175fe439993b
- Source dataset
- uspto-grants-1989_04
- Patent number
- US04820719
Reaction notes
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