Methyl iodide → 4,5-Dihydro-3,4,4-trimethyloxazolium iodide

HRID 2082602Notes

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]=1

Participants

Reactant 2

HCID 6328Methyl iodide

HCID 156174024,4-Dimethyl-2-[2-(8-phenyloctyl)phenyl]-4,5-dihydro-1,3-oxazole

Product 1

HCID 118173244,5-Dihydro-3,4,4-trimethyloxazolium iodide

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). 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-0803059088804ecdb313cc47845d397f
Source dataset: uspto-grants-1993_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05189226

Reaction notes

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