Dimethyl Sulfoxide → ethyl (1R,2R)-2-(3-iodophenyl)cyclopropanecarboxylate

HRID 1375669Notes

Reaction equation

HRID 1375669 reaction equation
[H-].[Na+].[I:3][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1.[CH3:17]S(C)=O>>[I:3][C:4]1[CH:5]=[C:6]([C@@H:10]2[CH2:17][C@H:11]2[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 15508352ethyl (2E)-3-(3-iodophenyl)acrylate

Product 1

HCID 86594116ethyl (1R,2R)-2-(3-iodophenyl)cyclopropanecarboxylate

Conditions

Temperature
65 °C

Procedure

Me3SOI (379 mg, 1.72 mmol) was suspended in 3 mL of DMSO. NaH (60% suspension in mineral oil, 70 mg, 1.72 mmol) was added. Stirred at room temperature before the 3-iodoethyl cinnamate (400 mg, 1.32 mmol) from Example 1A was added. The resulting mixture was heated at 65° C. for 20 minutes before it was stirred at room temperature for 2 hours. The resulting mixture was then worked up by partitioning between diethyl ether and water. The organic layer was washed with water and brine, dried over MgSO4, filtered, evaporated to provide the titled compound (127 mg, 31.8 mmol) as a light brown oil.

Workup

  1. additionwas added
  2. customby partitioning between diethyl ether and water
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0b85a4e541e34450a594817bc723c8fb
Source dataset
uspto-grants-2007_01
Patent number
US07169797B2

Reaction notes

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