Dichloromethane → HCID 68670764, compound

HRID 2070944Notes

Reaction equation

HRID 2070944 reaction equation
O[CH2:2][C:3]1[CH:4]=[C:5]([C:11](O)([CH3:13])[CH3:12])[C:6]([CH3:10])=[N:7][C:8]=1[CH3:9].C(Cl)[Cl:16]>>[Cl:16][CH2:2][C:3]1[C:8]([CH3:9])=[N:7][C:6]([CH3:10])=[C:5]([C:11]([CH3:13])=[CH2:12])[CH:4]=1

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 68670777HCID 68670777, compound

Product 1

HCID 68670764HCID 68670764, compound

Procedure

To a stirring solution of 2-(5-(hydroxymethyl)-2,6-dimethylpyridin-3-yl)propan-2-ol in 10 mL of CH2Cl2 was added 1.5 mL of SO2Cl2. After 11 h at r.t., the solution was concentrated and CH2Cl2 and 10 mL of sat. NaHCO3 solution were added, and the layers were separated. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. Purification by flash silica gel chromatography (20% Et2O/hexanes) provided 96.5 mg of the desired 3-(chloromethyl)-2,6-dimethyl-5-(prop-1-en-2-yl)pyridine as a mixture.

Workup

  1. concentrationthe solution was concentrated
  2. additionCH2Cl2 and 10 mL of sat. NaHCO3 solution were added
  3. customthe layers were separated
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification by flash silica gel chromatography (20% Et2O/hexanes)

Sources & evidence

ORD record
ord-74c2ebecbf054444940569c65eedfc13
Source dataset
uspto-grants-2012_10
Patent number
US08299267B2

Reaction notes

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