Hydrochloric Acid → HCID 13693403, compound

HRID 981254Notes

Reaction equation

HRID 981254 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH2:10][CH3:11])=[CH:5][CH:4]=1.Br[CH2:14][C:15]([O:17][CH3:18])=[O:16].Cl>C1(C)C=CC=CC=1.C1COCC1>[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:12])[CH:10]([CH3:11])[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 60984Methyl bromoacetateHCID 8211711-[4-(Methylthio)phenyl]-1-propanone

Product 1

HCID 13693403HCID 13693403, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of potassium hexamethylsilazane (0.158 mole) in toluene (254 ml) and THF (160 ml) at -78° C. was added dropwise the ketone from Step A of this Example (25.8 g) in THF (90 ml). The reaction mixture was stirred 30 minutes at -78° C. Methyl bromoacetate (16.2 ml) in THF (25 ml) was added dropwise. After stirring 1.5 hours at -78° C. the reaction mixture was poured into 1N HCl (400 ml). The organic layer was separated and the aqueous layer was further extracted with ethyl acetate. The combined organic layers were washed with water, dried over Na2SO4 and evaporated to give a yellow oil which was purified on a flash silica gel column (1 kg) using hexane/EtOAc (10:2) as eluant to give the title compound as an oil.

Workup

  1. stirringAfter stirring 1.5 hours at -78° C. the reaction mixture
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was further extracted with ethyl acetate
  4. washThe combined organic layers were washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated
  7. customto give a yellow oil which
  8. customwas purified on a flash silica gel column (1 kg)

Sources & evidence

ORD record
ord-497c5b9182ea41329cb5c39fc4e745e9
Source dataset
uspto-grants-1991_02
Patent number
US04990526

Reaction notes

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