Sulfoxonium, trimethyl-, iodide (1:1) → 1-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

HRID 1512622Notes

Reaction equation

HRID 1512622 reaction equation
[CH2:1]([Li])CCC.[I-].C[S+](C)(C)=O.[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:25]=[CH:24][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH:38]=[O:39])=[CH:28][CH:27]=3)=[CH:22][CH:21]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]>CS(C)=O>[CH2:12]([O:14][C:15]([C:17]1([C:20]2[CH:21]=[CH:22][C:23]([C:26]3[CH:31]=[CH:30][C:29]([C:32]4[O:36][N:35]=[C:34]([CH3:37])[C:33]=4[CH:38]4[CH2:1][O:39]4)=[CH:28][CH:27]=3)=[CH:24][CH:25]=2)[CH2:19][CH2:18]1)=[O:16])[CH3:13]

Participants

5

Reactant 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 866524021-[4'-(4-Formyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl esterHCID 178418339Butyllithium

Product 1

HCID 866524031-[4'-(3-Methyl-4-oxiranyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

n-Butyllithium (1.6 M in hexanes, 2.3 mL, 3.69 mmol) was dissolved in DMSO (8 mL). Trimethylsulfoxonium iodide (0.963 g, 4.29 mmol) was added, followed by 1-[4′-(4-formyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.46 g, 1.23 mmol) in DMSO (8 mL). The reaction was stirred at room temperature for 40 minutes and then poured over ice. The mixture was extracted three times with EtOAc, and the combined organic layers were washed three times with H2O, dried, and concentrated. The crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes) to give the title compound.

Workup

  1. additionpoured over ice
  2. extractionThe mixture was extracted three times with EtOAc
  3. washthe combined organic layers were washed three times with H2O
  4. customdried
  5. concentrationconcentrated
  6. customThe crude material was purified by silica gel chromatography (0-40% EtOAc in hexanes)

Sources & evidence

ORD record
ord-c201f86e6f324cefb221316984d1ad46
Source dataset
uspto-grants-2012_07
Patent number
US08217066B2

Reaction notes

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