Propionic Acid → HCID 66986270, compound

HRID 1254034Notes

Reaction equation

HRID 1254034 reaction equation
[C:1]([OH:5])(=[O:4])[CH2:2][CH3:3].C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[O:15]>CO>[C:1]([O:5][CH2:13][C:14]([C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)=[O:15])(=[O:4])[CH2:2][CH3:3]

Participants

5

Reactant 3

HCID 1032Propionic AcidHCID 10796Cesium carbonateHCID 7358232-Bromo-4'-(methylsulfonyl)acetophenone

Product 1

HCID 66986270HCID 66986270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

Propionic acid (1.5 mL, 20 mmol) was added over a period of 30 min to a stirred suspension of Cs2CO3 (3.30 g, 10 mmol) in MeOH (20 mL). The reaction mixture was concentrated and the residue was suspended in DMF (25 mL), to which was added 2-bromo-1-[4-(methylsulfonyl)phenyl]ethanone (5.00 g, 18 mmol). The mixture was stirred at 25° C. for 16 h, and then partitioned between H2O (100 mL) and EtOAc/hexane (20/100 mL). The organic layer was separated, washed with water (3×200 mL), dried over anhydrous Na2SO4, filtered and concentrated to give 2-[4-(methylsulfonyl)phenyl]-2-oxoethyl propionate. LCMS: [M+1]+=271.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between H2O (100 mL) and EtOAc/hexane (20/100 mL)
  3. customThe organic layer was separated
  4. washwashed with water (3×200 mL)
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-cc19122462d946b98506c93e9eaa1b79
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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