Sodium Hydroxide → HCID 69685469, compound

HRID 1700048Notes

Reaction equation

HRID 1700048 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-:7].[Na+].[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[CH2:17][C:18](=O)[CH:19]=[CH2:20]>CS(C)=O>[F:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:11]=1[C@@H:17]1[CH2:2][C@H:18]1[C:19](=[O:7])[CH3:20]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 18366203HCID 18366203, compound

Product 1

HCID 69685469HCID 69685469, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet and addition funnel was charged 2.47 g (11.2 mmoles) of trimethyl sulfoxonium iodide, 0.448 g (11.2 mmole) of powdered sodium hydroxide, and 50 mls DMSO. The mixture was stirred at room temperature for 0.5 hour, followed by the rapid addition of 2.04 g (11.2 mmole) 2,6-difluoro-phenyl-3-buten-2-one in 25 ml DMSO in one portion. The reaction was stirred for 15 minutes at ambient temperature, poured into 200 mls of ice water, and then extracted with 150 ml of ethyl ether. The ether extract was washed with 4×100 mls of water, dried over anhydrous MgSO4, filtered, and concentrated in vacuuo on a rotary evaporator to afford 1.3 g crude product as a yellow oil. This was combined with 1.6 g from a similar reaction and the total crude of 2.9 g was chromatographed on silica with CH2Cl2. Fractions (#5-9) were combined and concentrated in vacuuo on a rotary evaporator to afford 1.5 g (92% purity by GC) of trans-1-(2,6 difluorophenyl)-2-acetylcyclopropane as a free flowing pale yellow liquid, in 28.8% yield.

Workup

  1. customTo a 500 ml round bottom flask equipped with magnetic stirrer, nitrogen inlet and addition funnel
  2. stirringThe reaction was stirred for 15 minutes at ambient temperature
  3. extractionextracted with 150 ml of ethyl ether
  4. extractionThe ether extract
  5. washwas washed with 4×100 mls of water
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuuo on a rotary evaporator
  9. customto afford 1.3 g crude product as a yellow oil
  10. customThis was combined with 1.6 g from a similar reaction
  11. customthe total crude of 2.9 g was chromatographed on silica with CH2Cl2
  12. concentrationconcentrated in vacuuo on a rotary evaporator

Sources & evidence

ORD record
ord-d30d8245e2b2467282399def0cc0e8e1
Source dataset
uspto-grants-2002_02
Patent number
US06348627B1

Reaction notes

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