Water → 2-(1-Fluoro-4-pentynyl)-4,5-dihydro-4,4-dimethyloxazole

HRID 615551Notes

Reaction equation

HRID 615551 reaction equation
[F:1][CH:2]([CH2:6][CH2:7][C:8]#[CH:9])[C:3]([OH:5])=O.[NH2:10][C:11]([CH3:15])([CH3:14])[CH2:12]O.O>C1(C)C(C)=CC=CC=1>[F:1][CH:2]([C:3]1[O:5][CH2:12][C:11]([CH3:15])([CH3:14])[N:10]=1)[CH2:6][CH2:7][C:8]#[CH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 118072-Amino-2-methyl-1-propanolHCID 130449502-Fluorohex-5-ynoic acid

Product 1

HCID 130449512-(1-Fluoro-4-pentynyl)-4,5-dihydro-4,4-dimethyloxazoleYield 57%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 2-fluoro-5-hexynoic acid (3.0 g, 23.05 mmol) and 2-amino-2-methyl-1-propanol (2.05 g, 23.05 mmol) in 150 ml of dry xylene was refluxed for 16 h. The water formed during the reaction was removed by Linde 3A molecular sieves (15 g) contained in a continuous extractor. The xylene was then distilled off at atmospheric pressure, and the resulting pot material was taken into ether (100 ml). The ethereal solution was washed with saturated sodium bicarbonate solution, water, and dried over MgSO4. Evaporation of ether at 35° C./~ 35 mm, and distillation of the resulting crude product gave 2.4 g (57%) of 2-(1-fluoro-4-pentynyl)-4,5-dihydro-4,4-dimethyloxazole as a colorless liquid, bp 62°-66° C./0.6 mmHg.

Workup

  1. temperaturewas refluxed for 16 h
  2. customwas removed by Linde 3A molecular sieves (15 g)
  3. distillationThe xylene was then distilled off at atmospheric pressure
  4. washThe ethereal solution was washed with saturated sodium bicarbonate solution, water
  5. dry with materialdried over MgSO4
  6. customEvaporation of ether at 35° C./
  7. distillation~ 35 mm, and distillation of the resulting crude product

Sources & evidence

ORD record
ord-ee74e9994e4c41a6badea73354880bbb
Source dataset
uspto-grants-1985_02
Patent number
US04500462

Reaction notes

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