Sulfoxonium, trimethyl-, iodide (1:1) → Ethyl 1-[2,6-bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarboxylate

HRID 1484630Notes

Reaction equation

HRID 1484630 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[CH3:7][O:8][CH2:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([O:18][CH2:19][O:20][CH3:21])[C:12]=1[C:22](=[CH2:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24]>CS(C)=O>[CH3:7][O:8][CH2:9][O:10][C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[C:13]([O:18][CH2:19][O:20][CH3:21])[C:12]=1[C:22]1([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:2][CH2:28]1

Participants

4

Reactant 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67958720Ethyl 2-[2,6-bis(methoxymethoxy)-3-methyl-phenyl]prop-2-enoate2×

Product 1

HCID 67958381Ethyl 1-[2,6-bis(methoxymethoxy)-3-methyl-phenyl]cyclopropanecarboxylateYield 84.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of trimethylsulfoxonium iodide (4.4 g, 20 mmol) in dry dimethyl sulfoxide (30 mL) sodium hydride (60% dispersion in mineral oil) (0.720 g, 18 mmol) was added and the reaction mixture was stirred for 1 hour at room temperature. A solution of ethyl 2-[2,6-bis(methoxymethoxy)-3-methyl-phenyl]prop-2-enoate (Intermediate 9, 3.5 g, 11.29 mmol) in dry dimethyl sulfoxide (15 mL) was slowly added and the reaction mixture was stirred for 1 hour at room temperature. The reaction was quenched with an aqueous saturated solution of ammonium chloride (10 ml), diluted with water (40 ml) and extracted with ethyl acetate (2×100 ml). The organic layer was washed with water (2×50 ml), dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents affording the title compound (3.1 g) as a colourless oil.

Workup

  1. stirringthe reaction mixture was stirred for 1 hour at room temperature
  2. customThe reaction was quenched with an aqueous saturated solution of ammonium chloride (10 ml)
  3. additiondiluted with water (40 ml)
  4. extractionextracted with ethyl acetate (2×100 ml)
  5. washThe organic layer was washed with water (2×50 ml)
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified by flash chromatography (Biotage system) on silica gel using a 100 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents

Sources & evidence

ORD record
ord-b5bcd0a55b1546409111dc2ead50a0fe
Source dataset
uspto-grants-2016_08
Patent number
US09422272B2

Reaction notes

Loading…