Dimethyl Carbonate → Methyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoate

HRID 922323Notes

Reaction equation

HRID 922323 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][C:14]([C:17](=[O:19])[CH3:18])=[CH:13][CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:20](=O)([O:23]C)[O:21][CH3:22]>CN(C=O)C>[CH2:3]([O:10][C:11]1[CH:12]=[CH:13][C:14]([C:17](=[O:19])[CH2:18][C:20]([O:21][CH3:22])=[O:23])=[CH:15][CH:16]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 24758Sodium hydrideHCID 2452261-[4-(Benzyloxy)phenyl]ethan-1-one

Product 1

HCID 58806802Methyl 3-(4-(benzyloxy)phenyl)-3-oxopropanoateYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirring suspension of NaH (3.7 g, 154.2 mmol) in DMF (25 mL) was added 1-[4-(benzyloxy)phenyl]ethanone (7 g, 31 mmol) at −5° C. and stirred for 30 min, then dim ethyl carbonate (13.5 g, 150 mmol, dissolved in DMF) was added at −5° C. slowly (exothermic) and warmed slowly to RT, stirred at RT for overnight. Reaction mass was quenched with ice cold water and extracted with ethyl acetate, organic layer was washed with water and brine dried over Na2SO4. The organic layer was concentrated to give the product (7 g, Yield: 92%): 1H NMR (300 MHz, CDCl3): δ 7.84-7.87 (d, 2H), 7.28-7.35 (m, 5H), 6.94-6.96 (d, 2H), 5.07 (s, 2H), 3.89 (s, 2H), 3.68 (s, 3H)

Workup

  1. stirringstirred at RT for overnight
  2. customReaction mass
  3. customwas quenched with ice cold water
  4. extractionextracted with ethyl acetate, organic layer
  5. washwas washed with water and brine
  6. dry with materialdried over Na2SO4
  7. concentrationThe organic layer was concentrated

Sources & evidence

ORD record
ord-f7b3e57d677a4dc9ace668673db28a1d
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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