Pyridine → 2,3-Dihydro-1-oxo-3-phenyl-1H-inden-6-yl acetate

HRID 331261Notes

Reaction equation

HRID 331261 reaction equation
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[C:24](OC(=O)C)(=[O:26])[CH3:25]>C(Cl)Cl.CCOC(C)=O>[C:24]([O:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 703075012,3-Dihydro-6-hydroxy-3-phenylinden-1-one

Product 1

HCID 703172342,3-Dihydro-1-oxo-3-phenyl-1H-inden-6-yl acetateYield 77%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,3-Dihydro-6-hydroxy-3-phenylinden-1-one (22.5 g, 100 mmol) obtained in Step 2 was placed into a flask and dissolved in CH2Cl2 (300 mL). To the solution at 0° C., pyridine (40 mL, 5.0 eq) and acetic anhydride (47 mL, 5.0 eq) were added dropwise. The mixture was stirred for 8 h at room temperature. The reaction mixture was diluted with EtOAc and washed with H2O. The organic layer was dried over MgSO4 and concentrated in vacuo to give the desired product (20.0 g, 77%).

Workup

  1. washwashed with H2O
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81ed5030ec0f49dc85e148b914b7501a
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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