Hydrochloric Acid → HCID 59541849, compound

HRID 2388301Notes

Reaction equation

HRID 2388301 reaction equation
O1[C:5]2([CH2:10][CH2:9][C:8]([C:11]3[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:7][CH2:6]2)[O:4]CC1.Cl>C(#N)C>[CH3:18][O:17][C:12]1[C:11]([C:8]2[CH2:9][CH2:10][C:5](=[O:4])[CH2:6][CH:7]=2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59541817HCID 59541817, compound

Product 1

HCID 59541849HCID 59541849, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 3-(1,4-Dioxa-spiro[4.5]dec-7-en-8-yl)-2-methoxy-pyridine (as prepared in the previous step, 211 mg, 0.854 mmol) in acetonitrile was added aqueous HCl (5 mL, 5 mmol, 1M). The mixture was stirred at room temperature until HPLC indicated consumption of starting material. The reaction mixture was poured onto saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2) to afford 4-(2-methoxy-pyridin-3-yl)-cyclohex-3-enone.

Workup

  1. customconsumption of starting material
  2. additionThe reaction mixture was poured onto saturated sodium bicarbonate solution
  3. extractionextracted with ethyl acetate
  4. washThe organic layer washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (SiO2, 0-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-ea570a3c625f4fe9b0e70a7751e13e2c
Source dataset
uspto-grants-2012_09
Patent number
US08269015B2

Reaction notes

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