3-Pyridinemethanol → HCID 22054312, compound

HRID 1830253Notes

Reaction equation

HRID 1830253 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49](O)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:58][CH2:57][O:56][CH2:55][CH2:54]1)=[O:52].[OH-].[Na+]>C1C=CC=CC=1>[CH3:40][O:41][C:42]1[C:43]([CH3:70])=[C:44]([C:61]([O:68][CH3:69])=[C:62]([O:66][CH3:67])[C:63]=1[O:64][CH3:65])[CH2:45][C:46]1[CH:47]=[CH:48][C:49]([O:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:50]([CH:59]=1)[C:51]([N:53]1[CH2:54][CH2:55][O:56][CH2:57][CH2:58]1)=[O:52]

Participants

7

Reactant 5

HCID 75103-PyridinemethanolHCID 11776TriphenylphosphineHCID 14798Sodium HydroxideHCID 5462977Diethyl azodicarboxylateHCID 22054155HCID 22054155, compound

Product 1

HCID 22054312HCID 22054312, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Pyridinemethanol (0.080 g, 0.731 mmol), triphenylphosphine (0.192 g, 0.731 mmol) and diethylazodicarboxylate (0.127 g, 0.731 mmol) were added to a benzene solution of N-[5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoyl]morpholine (0.210 g, 0.487 mmol) and the solution was stirred at room temperature for 12 hours. The reaction solution was poured into an aqueous 2N sodium hydroxide solution (15 ml) and then extracted with methylene chloride. The extract was washed with water and then dried, and the solvent was removed by distillation. The obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1.5:8.5) to obtain the titled compound (0.195 g, 0.374 mmol, 77%).

Workup

  1. extractionextracted with methylene chloride
  2. washThe extract was washed with water
  3. customdried
  4. customthe solvent was removed by distillation
  5. customThe obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=1.5:8.5)

Sources & evidence

ORD record
ord-e20d8e479e544d55ad5e750008e72d26
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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