Oxygen → HCID 18436240, compound

HRID 351324Notes

Reaction equation

HRID 351324 reaction equation
C(C=[CH:4][C:5]([O:7]C)=O)#N.[CH3:9][CH:10]([OH:12])[CH3:11].[OH:13]N1C(=O)C2=CC=CC=C2C1=O.O=O.[C:27](#[N:29])[CH3:28]>C([O-])(=O)C.[Co+2].C([O-])(=O)C>[C:27]([CH:28]1[C:10]([CH3:11])([CH3:9])[O:12][C:4](=[O:13])[CH:5]1[OH:7])#[N:29]

Participants

7

Reactant 5

HCID 977OxygenHCID 3776IsopropanolHCID 6342AcetonitrileHCID 10665N-HydroxyphthalimideHCID 136708HCID 136708, compound

Product 1

HCID 18436240HCID 18436240, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6277Cobalt diacetateCatalyst

Procedure

A mixture of 3 mmol of methyl 3-cyano-acrylate, 30 mmol of 2-propanol, 0.6 mmol of N-hydroxyphthalimide, 0.003 mmol of cobalt(II) acetate, 0.03 mmol of acetylacetonatocobalt(III), and 1 ml of acetonitrile was stirred at 70° C. in an oxygen atmosphere (1 atm) for 8 hours. A reaction mixture was subjected to column chromatography on a silica gel to yield β-cyano-α-hydroxy-γ,γ-dimethyl-γ-butyrolactone in a yield of 68%.

Sources & evidence

ORD record
ord-6cda2779ce3d46ec96ca4702610ed32d
Source dataset
uspto-grants-2007_02
Patent number
US07183423B1

Reaction notes

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