Ethanol → 2-[4-(trifluoromethoxy)phenyl]oxirane

HRID 990073Notes

Reaction equation

HRID 990073 reaction equation
[H-].[Na+].[I-].C[S+](C)(C)=O.[F:9][C:10]([F:21])([F:20])[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]=[O:17])=[CH:14][CH:13]=1.[CH2:22](O)C>CS(C)=O.C1COCC1>[F:9][C:10]([F:20])([F:21])[O:11][C:12]1[CH:19]=[CH:18][C:15]([CH:16]2[CH2:22][O:17]2)=[CH:14][CH:13]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)

Product 1

HCID 120441952-[4-(trifluoromethoxy)phenyl]oxirane

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of sodium hydride(1.54 g, 38.46 mmol) in 35 mL of dry DMSO was added, via a solid addition funnel, trimethylsulfoxonium iodide (7.84 g, 35.61 mmol) over 5 minutes. After H2 gas evolution ceases the cloudy solution was treated with a solution of 4-trifluoromethoxybenzaldehyde (4.96 g, 25.05 mmol) in 35 mL of THF over 15 minutes. After one hour, 1 mL of ethanol was slowly added, then the THF and ethanol were removed by rotary evaporation. The DMSO solution was poured into 100 mL of water and then extracted with dichloromethane(3×75 mL). The combined organic extracts were washed with dilute brine (2×75 mL), dried (Na2SO4), filtered, evaporated and purified by flash chromatography (silica gel, 10% ethyl acetate/hexane). This procedure afforded 1.95 g of the title compound as a colorless oil.

Workup

  1. additionwas added, via a solid addition funnel
  2. customthe THF and ethanol were removed by rotary evaporation
  3. additionThe DMSO solution was poured into 100 mL of water
  4. extractionextracted with dichloromethane(3×75 mL)
  5. washThe combined organic extracts were washed with dilute brine (2×75 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated
  9. custompurified by flash chromatography (silica gel, 10% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-1a14b22cb59447bfa64371acae4eb055
Source dataset
uspto-grants-2002_10
Patent number
US06458817B1

Reaction notes

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