Pyridinium chloride → HCID 135545348, compound

HRID 491751Notes

Reaction equation

HRID 491751 reaction equation
Cl.N1C=CC=CC=1.C[O:9][C:10]1[CH:11]=[C:12]([C:27](O)([CH3:29])[CH3:28])[C:13]2[O:17][C:16]([C:18]3[CH:23]=[CH:22][C:21]([O:24]C)=[CH:20][CH:19]=3)=[N:15][C:14]=2[CH:26]=1>O>[OH:24][C:21]1[CH:20]=[CH:19][C:18]([C:16]2[O:17][C:13]3[C:12]([C:27]([CH3:29])=[CH2:28])=[CH:11][C:10]([OH:9])=[CH:26][C:14]=3[N:15]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 10176127Pyridinium chlorideHCID 21907383HCID 21907383, compound

Product 1

HCID 135545348HCID 135545348, compoundYield 41.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyridine hydrochloride (400 mg) was heated to 190° C. To the melt was added 2-[5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole-7-yl]propan-2-ol (114 mg, 0.36 mmol) and the reaction was stirred for 2 h. The mixture was cooled to room temperature, dissolved in water and extracted with EtOAc. The organic layers were combined and washed with HCl (1N), water then brine and dried over MgSO4. Evaporation and purification by flash chromatography (50%-60% EtOAc/petroleum ether) gave (40 mg, 41% yield) of the product as a light red-brown solid, m.p. 225-228° C.; MS m/e 268 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washwashed with HCl (1N), water
  3. dry with materialbrine and dried over MgSO4
  4. customEvaporation and purification by flash chromatography (50%-60% EtOAc/petroleum ether)

Sources & evidence

ORD record
ord-ea781db06cb645b082da00eca114f883
Source dataset
uspto-grants-2009_05
Patent number
US07531564B2

Reaction notes

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