Diisopropyl Ether → HCID 21187339, compound

HRID 1383268Notes

Reaction equation

HRID 1383268 reaction equation
[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9][CH3:10])[C:5]=2[C:11](=[O:26])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:13]=2[S:22]([CH3:25])(=[O:24])=[O:23])[CH2:3][CH2:2]1.ClC1C=CC=C(C(OO)=[O:35])C=1.C(OCC)(=O)C.CCCCCC.C(OC(C)C)(C)C>ClCCl>[CH:1]1([C:4]2[O:8][N:7]=[C:6]([S:9]([CH3:10])=[O:35])[C:5]=2[C:11](=[O:26])[C:12]2[CH:17]=[CH:16][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:14][C:13]=2[S:22]([CH3:25])(=[O:23])=[O:24])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 7914Diisopropyl EtherHCID 70297m-Chloroperbenzoic acidHCID 21226206Ethyl acetate hexaneHCID 22342446HCID 22342446, compound

Product 1

HCID 21187339HCID 21187339, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1.0 g (2.5 mmol) 5-Cyclopropyl-3-methylsulfanyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole is dissolved in 12 ml dichloromethane. The solution is then cooled to a temperature of −5° C., and 0.62 g (70%, 2.5 mmol) m-chloroperbenzoic acid is added in portions. After 18 hours' agitation at a temperature of 0 to 5° C., the reaction mixture is diluted with dichloromethane and the resulting precipitate filtered off. The dichloromethane phase is successively extracted with 5% aqueous NaHCO3 solution, twice with water and 15% aqueous sodium chloride solution. After the organic phase has been separated off, it is dried over magnesium sulfate. The raw product obtained is subjected to flash chromatography on silica gel using ethyl acetate/hexane (first 1:1 then 2:1) as eluent. After stirring in a little diisopropylether, 0,8 g of 5-cyclopropyl-3-methylsulfinyl-4-(2-methanesulfonyl-4-trifluoromethylbenzoyl)isoxazole is obtained in the form of crystals with a melting point of 153-155° C. 1H-NMR (CDCl3, ppm): 0.96-1.16 (m, 2H), 1.2-1.36 (m, 1H), 1.32-1.4 (m, 2H), 3.12 (s, 3H), 3.32 (s, 3H), 7.72 (d, 1H), 8.05 (d, 1H), 8.41 (s, 1H).

Workup

  1. additionis added in portions
  2. filtrationthe resulting precipitate filtered off
  3. extractionThe dichloromethane phase is successively extracted with 5% aqueous NaHCO3 solution, twice with water and 15% aqueous sodium chloride solution
  4. customAfter the organic phase has been separated off
  5. dry with materialit is dried over magnesium sulfate
  6. customThe raw product obtained

Sources & evidence

ORD record
ord-762c2e8a88cc455383bb02435dcc67fa
Source dataset
uspto-grants-2001_07
Patent number
US06255251B1

Reaction notes

Loading…