Water → Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylate

HRID 907464Notes

Reaction equation

HRID 907464 reaction equation
[I-].C[S+](C)(C)=O.[CH3:7]C([O-])(C)C.[K+].[CH3:13][O:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[C:16]=1[C:23](=[CH2:29])[C:24]([O:26][CH2:27][CH3:28])=[O:25].O>CS(C)=O>[CH3:22][O:21][C:17]1[CH:18]=[CH:19][CH:20]=[C:15]([O:14][CH3:13])[C:16]=1[C:23]1([C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH2:7][CH2:29]1

Participants

6

Reactant 4

HCID 962WaterHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 23665647Potassium tert-butoxideHCID 57659400Ethyl 2-(2,6-dimethoxyphenyl)acrylate

Product 1

HCID 57659403Ethyl 1-(2,6-dimethoxyphenyl)cyclopropanecarboxylateYield 70%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To trimethylsulfoxonium iodide (32 g, 1.2 equiv) in DMSO (250 ml) was added ground KOt-Bu (17.62 g, 1.3 equiv) and this mixture was stirred at r.t. for 30 min. A solution of the styrene 17 (28.53 g, 121 mmol) in DMSO (55 ml) was then added and this mixture was stirred at r.t. for 3 h. The reaction was poured into water (1.0 L) mixed with sat. NHCl (350 ml). The product was extracted into hexane (2×300 ml) and this solution was washed with water and brine, dried over Na2SO4 and filtered through silica (400 ml). The product was then eluted with EtOAc/hexane 15 and 20% to yield 18 (21.1 g, 70%) as a colorless oil.

Workup

  1. stirringthis mixture was stirred at r.t. for 3 h
  2. additionmixed with sat. NHCl (350 ml)
  3. extractionThe product was extracted into hexane (2×300 ml)
  4. washthis solution was washed with water and brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered through silica (400 ml)
  7. washThe product was then eluted with EtOAc/hexane 15 and 20%

Sources & evidence

ORD record
ord-b292f3a4d9614aaca02030b845a14e3c
Source dataset
uspto-grants-2011_09
Patent number
US08013159B2

Reaction notes

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