Dimethylsulfoxonium methylide → Methyl 2-(4-cyclohexylphenyl)cyclopropanecarboxylate

HRID 446764Notes

Reaction equation

HRID 446764 reaction equation
[CH:1]1([C:7]2[CH:12]=[CH:11][C:10](/[CH:13]=[CH:14]/[C:15]([O:17][CH3:18])=[O:16])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:19]S(C)(=O)=C>CS(C)=O>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH:13]3[CH2:19][CH:14]3[C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:12]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 6396768Dimethylsulfoxonium methylideHCID 58358304(E)-methyl 3-(4-cyclohexylphenyl)acrylate

Product 1

HCID 58358302Methyl 2-(4-cyclohexylphenyl)cyclopropanecarboxylateYield 70.8%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (E)-methyl 3-(4-cyclohexylphenyl)acrylate (200 mg, 0.82 mmol) in DMSO (20 mL) was added freshly prepared Corey's reagent (92 mg, 0.98 mmol) at RT and stirred for 3 h. The reaction was quenched with cold water and then extracted with EtOAc (2×20 mL). The combined organic layers were dried over magnesium sulfate, filtered and then concentrated in vacuo to obtain crude product. The crude material was purified via silica gel column chromatography eluting with 5% EtOAc/95% hexanes to afford methyl 2-(4-cyclohexylphenyl)cyclopropanecarboxylate (150 mg, 47%) as a solid.

Workup

  1. customThe reaction was quenched with cold water
  2. extractionextracted with EtOAc (2×20 mL)
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto obtain crude product
  7. customThe crude material was purified via silica gel column chromatography
  8. washeluting with 5% EtOAc/95% hexanes

Sources & evidence

ORD record
ord-a9adf2ac06774ad5bee9ead93d52c88d
Source dataset
uspto-grants-2013_07
Patent number
US08481532B2

Reaction notes

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