Chloroform → HCID 59739554, compound

HRID 1192943Notes

Reaction equation

HRID 1192943 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[C:3]=1[C:9]([S:11]([C:14]1[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][N:15]=1)(=[O:13])=[O:12])=[CH2:10].[OH-].[Na+].[CH:23]([Cl:26])(Cl)[Cl:24]>[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.O>[Cl:24][C:23]1([Cl:26])[CH2:10][C:9]1([C:3]1[C:4]([F:8])=[CH:5][CH:6]=[CH:7][C:2]=1[F:1])[S:11]([C:14]1[CH2:18][C:17]([CH3:20])([CH3:19])[O:16][N:15]=1)(=[O:13])=[O:12]

Participants

6

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 59739544HCID 59739544, compound

Product 1

HCID 59739554HCID 59739554, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 962WaterSolvent2×

Procedure

3-[1-(2,6-Difluoro-phenyl)-ethenesulfonyl]-5,5-dimethyl-4,5-dihydroisoxazole (prepared according to Example P12) (purity 80%) (0.2 g, 0.53 mmol) and a catalytic amount of triethylbenzylammonium chloride were dissolved in chloroform (1 ml). A solution of sodium hydroxide (0.64 g, 16 mmol) in water (1 ml) was added dropwise. After stirring for 1.5 hours at room temperature the mixture was diluted with water and extracted several times with chloroform. The combined organic phases were washed with water, dried over magnesium sulfate and concentrated. The crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane) to give the product (Compound No. 1.45 of Table 27) as a light brown gum that slowly solidified (74 mg, 36% yield).

Workup

  1. extractionextracted several times with chloroform
  2. washThe combined organic phases were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude product was purified by chromatography on silica gel (eluent: ethyl acetate/hexane)
  6. customto give the product (Compound No. 1.45 of Table 27) as a light brown gum that

Sources & evidence

ORD record
ord-d990b7846b2b4f10aeb7c3e87000fb11
Source dataset
uspto-grants-2014_03
Patent number
US08680290B2

Reaction notes

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