N,N,N',N'-Tetramethylazodicarboxamide → HCID 68814169, compound

HRID 730027Notes

Reaction equation

HRID 730027 reaction equation
[C:1]1([CH:11](O)[CH3:12])[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.C(P(CCCC)CCCC)CCC.N(C(N(C)C)=O)=NC(N(C)C)=O>C1COCC1>[C:1]1([CH:11]([N:18]2[C:14](=[O:24])[C:15]3[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:17]2=[O:19])[CH3:12])[C:10]2[C:4]([CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 6809PhthalimideHCID 13831TributylphosphineHCID 68814812HCID 68814812, compound

Product 1

HCID 68814169HCID 68814169, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude 1-(azulen-1-yl)ethanol prepared in Example 72, Step A was dissolved in dehydrated THF (380 mL), and stirred with cooling on ice under nitrogen atmosphere. This reaction mixture was added with phthalimide (45.0 g, Kanto Kagaku), tri-n-butylphosphine (37.7 mL, Kanto Kagaku), and 1,1′-azobis(N,N′-dimethylformamide) (26.3 g, Midori Kagaku), and stirred at room temperature for 16 hours under nitrogen atmosphere. The solid was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was added with saturated aqueous sodium hydrogencarbonate, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=6:1), to obtain 16.8 g of the title compound.

Workup

  1. temperaturewith cooling on ice under nitrogen atmosphere
  2. stirringstirred at room temperature for 16 hours under nitrogen atmosphere
  3. customThe solid was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionThe residue was added with saturated aqueous sodium hydrogencarbonate
  6. extractionextracted with ethyl acetate
  7. washThe organic layer was washed with saturated brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customthe solvent was evaporated under reduced pressure
  10. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-4ab183ad67194a0c9753cf73d6050c4f
Source dataset
uspto-grants-2009_09
Patent number
US07582658B2

Reaction notes

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