N,N,N',N'-Tetramethylazodicarboxamide → HCID 22054297, compound

HRID 1830240Notes

Reaction equation

HRID 1830240 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][OH:8])=[CH:3][CH:2]=1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O.[CH3:34][O:35][C:36]1[C:37]([CH3:60])=[C:38]([C:51]([O:58][CH3:59])=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[CH2:39][C:40]1[CH:41]=[CH:42][C:43](O)=[C:44]([CH:49]=1)[C:45]([O:47][CH3:48])=[O:46].[OH-].[Na+]>C1C=CC=CC=1>[CH3:34][O:35][C:36]1[C:37]([CH3:60])=[C:38]([C:51]([O:58][CH3:59])=[C:52]([O:56][CH3:57])[C:53]=1[O:54][CH3:55])[CH2:39][C:40]1[CH:41]=[CH:42][C:43]([O:8][CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=2)=[C:44]([CH:49]=1)[C:45]([O:47][CH3:48])=[O:46]

Participants

7

Reactant 5

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 114724-HydroxymethylpyridineHCID 13831TributylphosphineHCID 14798Sodium HydroxideHCID 21919163HCID 21919163, compound

Product 1

HCID 22054297HCID 22054297, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Pyridinemethanol (0.232 g, 2.13 mmol), tri-n-butylphosphine (0.430 g, 2.13 mmol) and N,N,N′,N′-tetramethylazodicarboxamide (0.366 g, 2.13 mmol) were added to a benzene solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate (0.500 g, 1.33 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 (hexand:ethyl acetate=2:3) to obtain the titled compound (0.610 g, 1.31 mmol, 98%).

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 (hexand:ethyl acetate=2:3)

Sources & evidence

ORD record
ord-eda2a7cf670941a0966f3985a679dfee
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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