Hydrochloric Acid → HCID 20328679, compound

HRID 2223843Notes

Reaction equation

HRID 2223843 reaction equation
[CH:1]1([CH:7]=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:9][C:10](C)([O-])[CH3:11].[K+].C(Br)C=C.Cl>CN(C)C=O.O>[CH2:11]([C:1]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1)[CH:10]=[CH2:9]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 16275CyclohexanecarboxaldehydeHCID 23665647Potassium tert-butoxide

Product 1

HCID 20328679HCID 20328679, compoundYield 47.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of cyclohexane carbaldehyde (2.24 g) in N,N-dimethylformamide (30 mL) were added potassium tert-butoxide (2.70 g) and allyl bromide (4.33 mL) under ice cooling. The solution was stirred under ice cooling for 30 minutes. Water and 1N hydrochloric acid were then added to the solution, and it was extracted with diethyl ether. The organic layer was washed with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. To a solution of the resulting residue in ethanol (60 mL) was added sodium borohydride (567 mg) under ice cooling. The solution was stirred at room temperature for 16 hours. Acetic acid was added to the solution, and it was concentrated under reduced pressure. To the resulting residue was added saturated aqueous sodium bicarbonate solution, and it was extracted with diethyl ether. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1) to give the title compound (1.47 g).

Workup

  1. extractionwas extracted with diethyl ether
  2. washThe organic layer was washed with water and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. additionTo a solution of the resulting residue in ethanol (60 mL) was added sodium borohydride (567 mg) under ice cooling
  6. stirringThe solution was stirred at room temperature for 16 hours
  7. additionAcetic acid was added to the solution, and it
  8. concentrationwas concentrated under reduced pressure
  9. additionTo the resulting residue was added saturated aqueous sodium bicarbonate solution, and it
  10. extractionwas extracted with diethyl ether
  11. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-b600848c803e481aba235bdac063d262
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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