Diethyl Ether → HCID 123228626, compound

HRID 1844240Notes

Reaction equation

HRID 1844240 reaction equation
[I-].C[S+](C)(C)=O.[H-].[Na+].[CH2:9]([O:12][C:13]1[CH:18]=[CH:17][C:16](/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=1)[CH:10]=[CH2:11].[CH3:26]COCC>CS(C)=O.[Cl-].[Na+].O>[CH2:9]([O:12][C:13]1[CH:18]=[CH:17][C:16]([C@@H:19]2[CH2:26][C@H:20]2[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:15][CH:14]=1)[CH:10]=[CH2:11]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 10966372HCID 10966372, compound2×

Product 1

HCID 123228626HCID 123228626, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

Trimethylsulfoxonium iodide (3.98 g, 18.08 mmol) was added in small portions to a suspension of NaH [0.72 g (60% in mineral oil), 18.08 mmol] in dry DMSO (20 mL). The mixture was stirred until gas evolution ceased and a clear solution was formed (1.5 h). Then, a solution of ethyl(E)-ethyl 3-(4-(allyloxy)phenyl)acrylate (Intermediate E, 4.00 g, 17.22 mmol) in DMSO (10 mL) was trasferred via cannula and the reaction was stirred for additional 1 h. The mixture was poured into brine (150 mL) and extrated with Et2O (100 mL); the organic layer was washed with brine (150 mL), dried over anhydrous Na2SO4 and filtered. Removal of the solvent afforded a yellowish solid, that was purified by column chromatography on silica gel (10% EtOAc/Hexanes), affording 1.96 g of (trans)-ethyl 2-(4-(allyloxy)phenyl)cyclopropanecarboxylate [Rf=0.4 (10% EtOAc/Hexanes), white solid, 46% yield].

Workup

  1. customa clear solution was formed (1.5 h)
  2. stirringthe reaction was stirred for additional 1 h
  3. washthe organic layer was washed with brine (150 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customRemoval of the solvent
  7. customafforded a yellowish solid, that
  8. customwas purified by column chromatography on silica gel (10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-1bdf85d946604a209e6d5c1eb3cf082b
Source dataset
uspto-grants-2015_02
Patent number
US08946296B2

Reaction notes

Loading…