HCID 66742926, compound → HCID 66742723, compound

HRID 1431067Notes

Reaction equation

HRID 1431067 reaction equation
[CH3:1][C:2]1([CH3:16])[CH2:6][O:5][C:4]([C:7]2[C:12]([F:13])=[CH:11][C:10]([F:14])=[CH:9][C:8]=2F)=[N:3]1.[CH3:17][Mg]Br>O1CCCC1>[F:13][C:12]1[CH:11]=[C:10]([F:14])[CH:9]=[C:8]([CH3:17])[C:7]=1[C:4]1[O:5][CH2:6][C:2]([CH3:1])([CH3:16])[N:3]=1

Participants

4

Reactant 2

HCID 66742926HCID 66742926, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 66742723HCID 66742723, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (ice bath) solution of 4,4-dimethyl-2-(2,4,6-trifluorophenyl)-4,5-dihydrooxazole (16.8 g, 73.3 mmol) in dry tetrahydrofuran (150 ml) was added a solution of methyl magnesium bromide (73.3 ml, 3M in ether) via slow drop-wise addition. The mixture was stirred for 2 hours at 0° C. and then warmed to ambient over 6 hours. The reaction was carefully quenched via the addition a saturated aqueous solution of ammonium chloride (30 ml) and the material was taken up in water (200 ml) and ethyl acetate (150 ml), transferred to a separatory funnel and the organic phase was collected. The organic phase was washed with water (200 ml) and the ethyl acetate phase collected. The aqueous phases were back extracted with ethyl acetate (2×120 ml) and the organic phases were combined, dried over magnesium sulfate, filtered and concentrated in vacuo to provide the desired product as a light yellow oil (16.31 g). (M+H)+=226 m/e.

Workup

  1. additionvia slow drop-wise addition
  2. temperaturewarmed
  3. waitto ambient over 6 hours
  4. customThe reaction was carefully quenched via the addition a saturated aqueous solution of ammonium chloride (30 ml)
  5. customethyl acetate (150 ml), transferred to a separatory funnel
  6. customthe organic phase was collected
  7. washThe organic phase was washed with water (200 ml)
  8. customthe ethyl acetate phase collected
  9. extractionThe aqueous phases were back extracted with ethyl acetate (2×120 ml)
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2a7b23c80d184c95b8fc96b77c5db57e
Source dataset
uspto-grants-2015_01
Patent number
US08940741B2

Reaction notes

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