Sodium Hydroxide → HCID 22132435, compound

HRID 1856686Notes

Reaction equation

HRID 1856686 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([OH:11])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[OH-].[Na+].Cl[CH2:15][CH:16]([OH:25])[CH2:17][CH2:18][C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1>C(O)C.O>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([O:11][CH2:15][CH:16]([OH:25])[CH2:17][CH2:18][C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 91152732,3-Dihydro-1,4-benzodioxin-6-olHCID 22465338HCID 22465338, compound

Product 1

HCID 22132435HCID 22132435, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent2×

Procedure

A solution of benzo-1,4-dioxan-6-ol (0.15 g; Tetrahedron, 1995, 3197) in ethanol (20 ml) at room temperature was treated with a solution of sodium hydroxide (0.044 g) in water (5 ml) and was then heated at reflux. A solution of (±)-α-(chloromethyl)-3-pyridinepropanol (1.0 g) in ethanol (5 ml) was added dropwise to the latter and the resulting mixture heated at reflux for 1 hour. The reaction mixture was cooled and then water was added. The organic component was extracted with dichloromethane, the combined extracts dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with ethyl acetate to give an oil (0.100 g).

Workup

  1. temperaturewas then heated
  2. temperatureat reflux
  3. temperaturethe resulting mixture heated
  4. temperatureat reflux for 1 hour
  5. temperatureThe reaction mixture was cooled
  6. extractionThe organic component was extracted with dichloromethane
  7. dry with materialthe combined extracts dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by column chromatography over silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-abc48e78804a4765888faa582149794c
Source dataset
uspto-grants-2000_11
Patent number
US06143751

Reaction notes

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