Acetic Acid → HCID 68291892, compound

HRID 339820Notes

Reaction equation

HRID 339820 reaction equation
[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][NH:6][S:7]([CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)(=[O:9])=[O:8].C([Li])CCC.[CH3:28][C:29]([CH3:31])=[O:30].C(O)(=O)C>C1COCC1.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[CH:17][C:4]=1[CH2:5][NH:6][S:7]([CH:10]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:29]([OH:30])([CH3:31])[CH3:28])(=[O:9])=[O:8]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 180AcetoneHCID 68292276HCID 68292276, compoundHCID 178418339Butyllithium

Product 1

HCID 68291892HCID 68291892, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-78 °C

Procedure

Under inert gas, 2.00 g of N-(2,4-dimethoxybenzyl)-C-phenylmethanesulfonamide were initially charged in 40 ml of THF, and then, at a temperature of −78° C., 9.54 ml of a 1.5 N butyllithium 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 a solution of 2.01 ml of acetone in 4 ml of THF was added. The mixture was allowed to come to room temperature and stirred for 30 minutes. The reaction solution was admixed with 0.82 ml of acetic acid and 50 ml of ethyl acetate, and washed with 30 ml of a saturated aqueous sodium hydrogencarbonate solution and 30 ml of a saturated aqueous sodium chloride solution, and the organic phase was dried over Na2SO4 and concentrated by rotary evaporation. The residue (2.67 g) 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 30 ml of a saturated aqueous sodium hydrogencarbonate solution and 30 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 (2.67 g) was used in the next reaction without further purification

Sources & evidence

ORD record
ord-b6fc498ceb0345d7ba2a8491dc533064
Source dataset
uspto-grants-2014_11
Patent number
US08895547B2

Reaction notes

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