N,N,N',N'-Tetramethylazodicarboxamide → HCID 22054156, compound

HRID 1830239Notes

Reaction equation

HRID 1830239 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[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:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[C:44]([CH:49]=1)[C:45]([O:47][CH3:48])=[O:46]

Participants

7

Reactant 5

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 75103-PyridinemethanolHCID 13831TributylphosphineHCID 14798Sodium HydroxideHCID 21919163HCID 21919163, compound

Product 1

HCID 22054156HCID 22054156, compoundYield 69.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3-Pyridinemethanol (0.084 g, 0.774 mmol), tri-n-butylphosphine (0.156 g, 0.774 mmol) and N,N,N′,N′-tetramethylazodicarboxamide (0.133 g, 0.774 mmol) were added to a benzene solution of methyl 5-(3,4,5,6-tetramethoxy-2-methylbenzyl)-2-hydroxybenzoate (0.194 g, 0.516 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 (0.167 g, 0.358 mmol, 69%).

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-7dd89e93127a4670a081a684a57f16bb
Source dataset
uspto-grants-2006_06
Patent number
US07064124B2

Reaction notes

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