Methanol → HCID 15166496, compound

HRID 1734732Notes

Reaction equation

HRID 1734732 reaction equation
N1C=C([CH:7]=[O:8])C=CC=1.[CH3:9][C:10]1([CH3:32])[CH2:19][C:18]([CH3:21])([CH3:20])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]=[O:31])=[CH:26][N:25]=3)[CH:16]=2)[O:11]1.CO.O.[C:36]1(C)C=CC(S(O)(=O)=O)=CC=1>O.C1C=CC=CC=1>[CH3:9][C:10]1([CH3:32])[CH2:19][C:18]([CH3:20])([CH3:21])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:22]#[C:23][C:24]3[CH:29]=[CH:28][C:27]([CH:30]([O:8][CH3:7])[O:31][CH3:36])=[CH:26][N:25]=3)[CH:16]=2)[O:11]1

Participants

7

Reactant 4

HCID 887MethanolHCID 103713-PyridinecarboxaldehydeHCID 521998p-Toluenesulfonic acid monohydrateHCID 15166494HCID 15166494, compound

Product 1

HCID 15166496HCID 15166496, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 962WaterSolvent

Procedure

A round-bottomed flask is fitted with a Dean-stark apparatus under a reflux condenser protected by a drying tube. A mixture of 3.58 g (12 mmol) of 2-[2,2,4,4-tetramethyl-chroman-6-yl)-ethynyl]-pyridine-5-carboxaldehyde (Compound 52) 4.80 mg (15 mmol) of anhydrous methanol, 2 mg of p-toluenesulfonic acid monohydrate and 10 ml of anhydrous benzene is placed in the flask and the mixture heated at reflux under nitrogen until close to the theoretical amount of water is collected in the Dean-Stark trap. The reaction mixture is cooled to room temperature and extracted successively with 5 ml of 10% sodium hydroxide solution and two 5 ml portions of water and then dried (MgSO4). The solution is then filtered and the solvent removed in vacuo. The residue is purified by chromatography and then recrystallization to give the title compound.

Workup

  1. customA round-bottomed flask is fitted with a Dean-stark apparatus under a reflux condenser
  2. customprotected by a drying tube
  3. temperaturethe mixture heated
  4. temperatureat reflux under nitrogen
  5. customis collected in the Dean-Stark trap
  6. extractionextracted successively with 5 ml of 10% sodium hydroxide solution and two 5 ml portions of water
  7. dry with materialdried (MgSO4)
  8. filtrationThe solution is then filtered
  9. customthe solvent removed in vacuo
  10. customThe residue is purified by chromatography
  11. customrecrystallization

Sources & evidence

ORD record
ord-6605a2c44a7a4aa68d7c3aff934f3832
Source dataset
uspto-grants-1996_07
Patent number
US05534516

Reaction notes

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