Acetone → HCID 22262027, compound

HRID 1610558Notes

Reaction equation

HRID 1610558 reaction equation
[F:1][C:2]([F:18])([O:6][C:7]1[N:12]=[C:11]([C:13](OCC)=[O:14])[CH:10]=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4].COCCO[AlH2-]OCCOC.[Na+].CC(C)=O.O>O1CCCC1>[F:18][C:2]([F:1])([O:6][C:7]1[N:12]=[C:11]([CH2:13][OH:14])[CH:10]=[CH:9][CH:8]=1)[CH:3]([F:5])[F:4]

Participants

6

Reactant 4

HCID 180AcetoneHCID 962WaterHCID 16684438Red-AlHCID 22261495HCID 22261495, compound

Product 1

HCID 22262027HCID 22262027, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 6-(1,1,2,2-tetrafluoroethoxy)-pyridine-2-carboxylate (5.65 g, 21.2 mmol) in tetrahydrofuran (60 ml) was added Red-Al (registered trademark, 6.11 g, 21.2 mmol). The reaction solution was stirred at room temperature for 30 min. and acetone (2 ml) was added. Water (100 ml) was added to the reaction solution and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed successively with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl-acetate=4:1) to give the objective substance (4.2 g, 88%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 ml×2)
  2. washThe extract was washed successively with water and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl-acetate=4:1)
  6. customto give the objective substance (4.2 g, 88%)

Sources & evidence

ORD record
ord-6d8547376b7c4c79ad5e71c684020cc9
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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