Acetone → HCID 68293504, compound

HRID 2405690Notes

Reaction equation

HRID 2405690 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][C:15]=2[O:22][CH3:23])(=[O:11])=[O:10])=[CH:4][CH:3]=1.C[Li].[CH3:26][C:27]([CH3:29])=[O:28].FC(F)(F)C(O)=O>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:23][O:22][C:15]1[CH:16]=[C:17]([O:20][CH3:21])[CH:18]=[CH:19][C:14]=1[CH2:13][NH:12][S:9]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=1)[C:27]([OH:28])([CH3:29])[CH3:26])(=[O:10])=[O:11]

Participants

8

Reactant 4

HCID 180AcetoneHCID 6422Trifluoroacetic acidHCID 68292190HCID 68292190, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 68293504HCID 68293504, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Under inert gas, 28 g of C-(4-bromophenyl)-N-(2,4-dimethoxybenzyl)methanesulfonamide were initially charged in 250 ml of THF, and then, at a temperature of −78° C., 93 ml of a 1.6 N methyllithium solution in hexane were added dropwise and the mixture was left to stir while cooling with ice for 5 minutes. Subsequently, the reaction solution was cooled again to −78° C. and 20 ml of acetone were added. The mixture was allowed to come to room temperature and stirred for 30 minutes. The reaction solution was admixed with 13 ml of trifluoroacetic acid and 500 ml of ethyl acetate, and washed with 300 ml of a saturated aqueous sodium hydrogencarbonate solution and 300 ml of a saturated aqueous sodium chloride solution, and the organic phase was dried over Na2SO4 and concentrated by rotary evaporation. The residue was used in the next reaction without further purification.

Workup

  1. waitthe mixture was left
  2. temperaturewhile cooling with ice for 5 minutes
  3. customto come to room temperature
  4. stirringstirred for 30 minutes
  5. washwashed with 300 ml of a saturated aqueous sodium hydrogencarbonate solution and 300 ml of a saturated aqueous sodium chloride solution
  6. dry with materialthe organic phase was dried over Na2SO4
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-c8040eaea21b44d4987ecf18f9e9d253
Source dataset
uspto-grants-2014_08
Patent number
US08809324B2

Reaction notes

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