Tetrahydrofuran → HCID 86666291, compound

HRID 1026282Notes

Reaction equation

HRID 1026282 reaction equation
[F:1][CH:2]([F:16])[CH:3]([OH:15])[CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:8][N:7]=1.[CH3:17][S:18](Cl)(=[O:20])=[O:19].C(N(CC)CC)C.C1COCC1>O>[F:16][CH:2]([F:1])[CH:3]([O:15][S:18]([CH3:17])(=[O:20])=[O:19])[CH2:4][O:5][C:6]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[O:8][N:7]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67777697HCID 67777697, compound

Product 1

HCID 86666291HCID 86666291, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of methyl 3-(3,3-difluoro-2-hydroxypropoxy)isoxazole-5-carboxylate (370 mg), methanesulfonyl chloride (0.362 mL), triethylamine (0.652 mL) and THF (10 mL) was stirred at 0° C. for 1 hr, and then at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a colorless oil (432 mg).

Workup

  1. customat room temperature
  2. customovernight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-063c1edba7cd4f5d8c9db33ad33723dd
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…