Potassium Carbonate → HCID 55066211, compound

HRID 870520Notes

Reaction equation

HRID 870520 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=1[O:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].I[CH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1>CC(C)=O>[CH3:11][O:10][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:2]=1[O:1][CH2:19][CH:20]1[CH2:25][CH2:24][O:23][CH2:22][CH2:21]1)[C:6]#[N:7]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 781354-Hydroxy-3-methoxybenzonitrileHCID 27955074-(Iodomethyl)oxane

Product 1

HCID 55066211HCID 55066211, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

1.0 g 4-Hydroxy-3-methoxybenzonitrile, 1.1 g potassium carbonate and 2.0 g 4-(iodomethyl)-tetrahydropyran were placed in 20 mL acetone and heated to reflux overnight. After this time, 1.1 g potassium carbonate was added and the reaction was heated at reflux for a further 2 h before more 0.93 g potassium carbonate was introduced and reflux was continued for a further 3 h. The mixture was then cooled to ambient temperature and concentrated under reduced pressure. The material that remained was partitioned between diethyl ether and water and the aqueous phase was removed and extracted with additional diethyl ether. The combined organic fractions were dried, filtered and the filtrate was concentrated under reduced pressure. Purification by silica gel chromatography (SiO2: ethyl acetate/heptanes: 10% to 30%) provided the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperaturethe reaction was heated
  4. additionwas introduced
  5. temperaturereflux
  6. concentrationconcentrated under reduced pressure
  7. customThe material that remained was partitioned between diethyl ether and water
  8. customthe aqueous phase was removed
  9. extractionextracted with additional diethyl ether
  10. customThe combined organic fractions were dried
  11. filtrationfiltered
  12. concentrationthe filtrate was concentrated under reduced pressure
  13. customPurification by silica gel chromatography (SiO2: ethyl acetate/heptanes: 10% to 30%)

Sources & evidence

ORD record
ord-3e3da1b863004a879b538a157dda3622
Source dataset
uspto-grants-2015_03
Patent number
US08969568B2

Reaction notes

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