Acetic Anhydride → HCID 21253079, compound

HRID 1530835Notes

Reaction equation

HRID 1530835 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:9]([N+:12]([O-])=O)=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:15](=[O:17])[CH3:16])[CH2:7]2.[H][H].[C:20](OC(=O)C)(=[O:22])[CH3:21]>C1COCC1.[Ni]>[C:15]([N:6]1[CH2:5][CH2:4][C:3]2[C:8](=[C:9]([NH:12][C:20](=[O:22])[CH3:21])[CH:10]=[CH:11][C:2]=2[Br:1])[CH2:7]1)(=[O:17])[CH3:16]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 21253086HCID 21253086, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21253079HCID 21253079, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

The product from Example 2 (13.05 g, 43.6 mmol) was dissolved in THF (100 mL) and treated with Raney Nickel (2 g). Under the presence of hydrogen (19.8 psi, 23° C.) the mixture was stirred for 19 hours, and evaporated under vacuum. The residue was then washed with diethyl ether and evaporated under vacuum to give a semi-solid. The semi-solid was treated with acetic anhydride (30 mL), THF (30 mL) and stirred. After 2 hours the solvent was evaporated under vacuum. The residue was dissolved in THF, dried with MgSO4, activated charcoal, and passed through a plug of silica gel eluted with ethyl acetate. Upon evaporation under vacuum the desired product was isolated (14.6 g, 96% yield) as a tan solid, mp=127-130° C.

Workup

  1. customevaporated under vacuum
  2. washThe residue was then washed with diethyl ether
  3. customevaporated under vacuum
  4. customto give a semi-solid
  5. customAfter 2 hours the solvent was evaporated under vacuum
  6. dissolutionThe residue was dissolved in THF
  7. dry with materialdried with MgSO4, activated charcoal
  8. washeluted with ethyl acetate
  9. customUpon evaporation under vacuum the desired product
  10. customwas isolated (14.6 g, 96% yield) as a tan solid, mp=127-130° C.

Sources & evidence

ORD record
ord-16c1b8a87d74482da3b2ae10c4267a29
Source dataset
uspto-grants-2001_03
Patent number
US06197771B1

Reaction notes

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