Acetic Anhydride → 1-[4-(Morpholine-4-sulfonyl)-3-trifluoromethyl-phenyl]-ethanone

HRID 1098748Notes

Reaction equation

HRID 1098748 reaction equation
C([Mg]Cl)(C)C.Br[C:7]1[CH:12]=[CH:11][C:10]([S:13]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)(=[O:15])=[O:14])=[C:9]([C:22]([F:25])([F:24])[F:23])[CH:8]=1.[C:26](OC(=O)C)(=[O:28])[CH3:27].C([O-])(O)=O.[Na+]>C1COCC1.C(OCC)(=O)C.O>[N:16]1([S:13]([C:10]2[CH:11]=[CH:12][C:7]([C:26](=[O:28])[CH3:27])=[CH:8][C:9]=2[C:22]([F:25])([F:24])[F:23])(=[O:15])=[O:14])[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1

Participants

8

Reactant 4

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 473151804-(4-Bromo-2-trifluoromethyl-benzenesulfonyl)-morpholineHCID 178418918HCID 178418918, compound

Product 1

HCID 595062911-[4-(Morpholine-4-sulfonyl)-3-trifluoromethyl-phenyl]-ethanoneYield 44.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of isopropylmagnesium chloride (2M in THF, 10 ml, 20.04 mmol) was added drop wise to a solution of the product obtained in step 1 (5.00 g, 13.36 mmol) in THF (30 ml) at −10° C. The mixture was stirred at this temperature for 1 h and then added drop wise to acetic acid anhydride (12.6 ml, 133.60 mmol) at −15° C. The reaction mixture was stirred at 0° C. for 2 h and allowed to warm up slowly to RT. Water (100 ml) was added and the reaction mixture was stirred at 60° C. for 15 min. The mixture was diluted with ethyl acetate at RT, neutralized with aqueous NaHCO3, washed with brine, dried over sodium sulphate and evaporated. Purification of the crude product by silica gel chromatography using ethyl acetate/n-heptane gave the desired product (2.00 g, 44%).

Workup

  1. stirringThe reaction mixture was stirred at 0° C. for 2 h
  2. stirringthe reaction mixture was stirred at 60° C. for 15 min
  3. washwashed with brine
  4. dry with materialdried over sodium sulphate
  5. customevaporated
  6. customPurification of the crude product by silica gel chromatography

Sources & evidence

ORD record
ord-27884c8f32cb4432aceb1087f90ab2a6
Source dataset
uspto-grants-2012_03
Patent number
US08143242B2

Reaction notes

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