Ethyl phenylacetate → Dimethyl 1-(4-methoxyphenyl)-1,2-cyclopropanedicarboxylate

HRID 2265067Notes

Reaction equation

HRID 2265067 reaction equation
[H-].[Na+].Br[CH:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[C:17]1([CH2:23][C:24]([O:26][CH2:27]C)=[O:25])C=CC=CC=1.C(OCC)(=O)C=C>CCOCC.C(OC)(=O)C=C.O.CO>[CH3:16][O:15][C:12]1[CH:13]=[CH:14][C:9]([C:4]2([C:5]([O:7][CH3:8])=[O:6])[CH2:17][CH:23]2[C:24]([O:26][CH3:27])=[O:25])=[CH:10][CH:11]=1

Participants

9

Reactant 4

HCID 7590Ethyl phenylacetateHCID 8821Ethyl AcrylateHCID 24758Sodium hydride2×HCID 10753737Methyl 2-bromo-2-(4-methoxyphenyl)acetate

Product 1

HCID 59468695Dimethyl 1-(4-methoxyphenyl)-1,2-cyclopropanedicarboxylate

Reagents, catalysts & solvents 4

HCID 887MethanolSolvent3×HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 7294Methyl AcrylateSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred slurry of of NaH (4.4 g, 60% in mineral oil) in anhydrous Et2O (0.3 l) was added methanol (10.3 mL) followed by a solution of bromo ester obtained in Prep. 1 methyl bromo(4-methoxyphenyl)acetate (29 g) in methyl acrylate (19.8 mL) (for examples starting from an ethyl phenylacetate derivative ethanol and ethyl acrylate were used, respectively) and methanol (3 mL) at 0° C., over a 30 min. The mixture was stirred at 25° C. for 24 h and then unreacted NaH was decomposed with 3 mL methanol. Water was added (75 mL), the organic phase separated, dried over Na2SO4 and filtered. Volatiles were evaporated in vacuo to give 31.5 g of the title compound as an oil, which was used in the subsequent step without further purification.

Workup

  1. customobtained in Prep
  2. customthe organic phase separated
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customVolatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-9b8a6547a657470186961188f377386f
Source dataset
uspto-grants-2010_12
Patent number
US07855298B2

Reaction notes

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