Acetone → HCID 68292295, compound

HRID 339866Notes

Reaction equation

HRID 339866 reaction equation
COC1C=C(OC)C=CC=1C[NH:6][S:7]([CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:11])(=[O:9])=[O:8].C([Li])CCC.[CH3:29][C:30]([CH3:32])=[O:31].FC(F)(F)C(O)=O>C1COCC1.CCCCCC.C(OCC)(=O)C.O>[OH:31][C:30]([CH3:32])([CH3:29])[C:10]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([S:7]([NH2:6])(=[O:8])=[O:9])[CH3:11]

Participants

9

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68291851HCID 68291851, compoundHCID 178418339Butyllithium

Product 1

HCID 68292295HCID 68292295, compound

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

Under inert gas, 330 mg of N-(2,4-dimethoxybenzyl)-1-phenylethanesulfonamide were initially charged in 5 ml of THF, and then, at a temperature of −78° C., 1.41 ml of a 1.6 N butyllithium solution in hexane were added dropwise and the mixture was stirred for 5 minutes. Subsequently, 0.22 ml of acetone was added, the mixture was stirred briefly and, after the addition of 1 ml of trifluoroacetic acid, the reaction solution was allowed to come to room temperature. The reaction mixture was admixed with 50 ml of water and 50 ml of ethyl acetate, and the aqueous phase was reextracted with 50 ml of ethyl acetate. The combined organic phases were dried over MgSO4 and concentrated by rotary evaporation, and the residue was purified by means of normal phase chromatography using a Flashmaster with an n-heptane/ethyl acetate gradient. The product-containing fractions were combined and concentrated by rotary evaporation. This gave the product (113 mg) with a molecular weight of 243.3 g/mol (C11H7NO3S).

Workup

  1. stirringthe mixture was stirred briefly
  2. customto come to room temperature
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. customthe residue was purified by means of normal phase chromatography
  6. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-7fb3fcc96a7d4b839029956679c7a720
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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