Hydrochloric Acid → Ethyl trans-2-(3-Methoxyphenyl)cyclopropanecarboxylate

HRID 377316Notes

Reaction equation

HRID 377316 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH2:8]([O:10][C:11](/[CH:13]=[CH:14]/[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[O:12])[CH3:9].Cl>CN(C)C=O.C(OCC)(=O)C>[CH2:8]([O:10][C:11]([C@@H:13]1[CH2:4][C@H:14]1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1)=[O:12])[CH3:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 5373781Ethyl (2E)-3-(3-methoxyphenyl)-2-propenoate

Product 1

HCID 54192159Ethyl trans-2-(3-Methoxyphenyl)cyclopropanecarboxylateYield 18%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of sodium hydride (1.0 g, 60% in oil) in N,N-dimethylformamide (50 ml) was added trimethylsulfonium iodide (6.1 g) at ambient temperature under N2 and stirred for 20 minutes. To the solution was added dropwise a solution of trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)ethylene (5.2 g) in N,N-dimethylformamide (10 ml) and stirred for 2 hours. The reaction mixture was poured into a mixture of ethyl acetate (100 ml) and 1N-hydrochloric acid (100 ml). The organic layer was washed with water, saturated sodium bicarbonate aqueous solution, and brine, and then dried over magnesium sulfate. The solution was evaporated and the residue was chromatographed (hexane:ethyl acetate=4:1) to give trans-1-ethoxycarbonyl-2-(3-methoxyphenyl)cyclopropane (1.0 g).

Workup

  1. stirringstirred for 2 hours
  2. washThe organic layer was washed with water, saturated sodium bicarbonate aqueous solution, and brine
  3. dry with materialdried over magnesium sulfate
  4. customThe solution was evaporated
  5. customthe residue was chromatographed (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-cb7244ae0f124433a4a1b6a5a66d15ce
Source dataset
uspto-grants-2000_02
Patent number
US06025375

Reaction notes

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