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

HRID 2108072Notes

Reaction equation

HRID 2108072 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

3

Reactant 2

HCID 6328Methyl iodideHCID 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

  1. customRemoval of the volatiles

Sources & evidence

ORD record
ord-c3bd394fb8554fa69d85af1404a866f0
Source dataset
uspto-grants-1990_06
Patent number
US04937253

Reaction notes

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