Pyridine → HCID 68738533, compound

HRID 448193Notes

Reaction equation

HRID 448193 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8](=[O:10])[CH3:9])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:19]=1[C:20](Cl)=[O:21]>C(Cl)Cl>[CH3:17][C:18]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[C:19]=1[C:20]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8](=[O:10])[CH3:9])[CH:3]=1)=[O:21]

Participants

5

Reactant 3

HCID 1049PyridineHCID 84873-HydroxyacetophenoneHCID 890962,6-Dimethylbenzoyl chloride

Product 1

HCID 68738533HCID 68738533, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 3′-Hydroxyacetophenone (4.84 g, 35.5 mmol) in anhydrous CH2Cl2 (50 ml) was added at room temperature pyridine (25 ml) followed by addition of 2,6-Dimethylbenzoyl chloride (Step A, 6 g, 35 mmol) in anhydrous CH2Cl2 (10 ml) under argon. The reaction mixture was stirred for 16 hours, concentrated under reduced pressure, diluted with CH2Cl2, and washed with 0.1M HCl, water and brine. The organic layer was dried over Na2SO4, concentrated and purified by flash chromatography eluted with ethyl acetate:hexane (1:2) to give the title compound.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additiondiluted with CH2Cl2
  3. washwashed with 0.1M HCl, water and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography
  7. washeluted with ethyl acetate:hexane (1:2)

Sources & evidence

ORD record
ord-81103bde3acf4accb36a3c2f4a275294
Source dataset
uspto-grants-2013_07
Patent number
US08481595B2

Reaction notes

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