Sodium Bicarbonate → HCID 71663143, compound

HRID 2178141Notes

Reaction equation

HRID 2178141 reaction equation
[F:1][C:2]([F:11])([F:10])[CH:3]1[O:7][N:6]=[C:5]([CH2:8]O)[CH2:4]1.O1CCN(S(F)(F)[F:19])CC1.C([O-])(O)=O.[Na+]>ClCCl>[F:19][CH2:8][C:5]1[CH2:4][CH:3]([C:2]([F:11])([F:10])[F:1])[O:7][N:6]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2733258Morpholinosulfur trifluorideHCID 71662966HCID 71662966, compound

Product 1

HCID 71663143HCID 71663143, compoundYield 35.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of crude (5-(trifluoromethyl)-4,5-dihydroisoxazol-3-yl)methanol (7.0 g, 41.4 mmol) in dichloromethane (140 ml) was added at −78° C. morpholinosulfur trifluoride (7.98 g, 45.5 mmol) and stirring was continued at −78° C. for 15 min, at 0° C. for 1 h and at 22° C. for 30 min. The solution was treated with cold aqueous NaHCO3, the organic layer was dried, evaporated (70 mbar/40° C.) and the residue was distilled from bulb to bulb at 100° C./0.8 mbar to give 3-(fluoromethyl)-5-(trifluoromethyl)-4,5-dihydroisoxazole (2.54 g) as a pale yellow liquid. MS: m/z=171 [M]+.

Workup

  1. customthe organic layer was dried
  2. customevaporated (70 mbar/40° C.)
  3. distillationthe residue was distilled from bulb to bulb at 100° C./0.8 mbar

Sources & evidence

ORD record
ord-814ffa8f4e0847429689ac4c4a01d11b
Source dataset
uspto-grants-2015_06
Patent number
US09067926B2

Reaction notes

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