Sulfoxonium, trimethyl-, iodide (1:1) → Ethyl 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)cyclopropanecarboxylate

HRID 1505436Notes

Reaction equation

HRID 1505436 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[CH3:7][O:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH2:18][O:19][CH3:20])[C:12]=1[C:21](=[CH2:27])[C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O>[CH3:20][O:19][CH2:18][O:17][C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([O:10][CH2:9][O:8][CH3:7])[C:12]=1[C:21]1([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:2][CH2:27]1

Participants

4

Reactant 2

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67235183Ethyl 2-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-propenoate2×

Product 1

HCID 67235562Ethyl 1-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)cyclopropanecarboxylateYield 80.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of trimethylsulfoxonium iodide (1.805 g, 8.20 mmol) in dry dimethyl sulfoxide (20 mL) sodium hydride 60% dispersion in mineral oil (0.310 g, 7.75 mmol) was added and the reaction mixture was stirred for 1 hour at room temperature. A solution of ethyl 2-(2,6-bis{[(methyloxy)methyl]oxy}phenyl)-2-propenoate (Reference Intermediate 210, 1.35 g) in dry dimethyl sulfoxide (10 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 (20 ml) and extracted with ethyl acetate (2×50 ml). The organic layer was washed with water (50 ml), dried over sodium sulphate, filtered and evaporated. The residue was purified by flash chromatography (Biotage system) on silica gel using a 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents affording the title as a colourless oil (1.14 g).

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 (20 ml)
  4. extractionextracted with ethyl acetate (2×50 ml)
  5. washThe organic layer was washed with water (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 50 g SNAP column and cyclohexane to cyclohexane/ethyl acetate 8:2 as eluents

Sources & evidence

ORD record
ord-1b795fab025c400cb0c199042da8dfb0
Source dataset
uspto-grants-2015_12
Patent number
US09216967B2

Reaction notes

Loading…