Sulfuric Acid → 3-(3-Cyano-thiophen-2-yl)-3-oxo-propionic acid

HRID 1745549Notes

Reaction equation

HRID 1745549 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8](Cl)=[O:9])#[N:2].C[Si]([C:15]([Si](C)(C)C)([C:19]([O-:21])=[O:20])[C:16]([O-:18])=[O:17])(C)C.CCN([CH2:31][CH3:32])CC.[Li+].[Br-].OS(O)(=O)=O.[CH3:40]C#N>C(OC(C)=C)(=O)C>[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8](=[O:9])[CH2:15][C:16]([OH:18])=[O:17])#[N:2].[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[O:9][C:31]([CH3:32])([CH3:40])[O:21][C:19](=[O:20])[CH:15]=1)#[N:2]

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8471TriethylamineHCID 82050Lithium BromideHCID 222245802,2-Bis(trimethylsilyl)propanedioateHCID 222247493-Cyanothiophene-2-carbonyl chloride

Product 2

HCID 222249153-(3-Cyano-thiophen-2-yl)-3-oxo-propionic acidHCID 222249166-(3-Cyano-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

The 3-(3-cyano-thiophen-2-yl)-3-oxo-propionic acid was prepared from 3-cyano-thiophene-2-carbonyl chloride (24.33 g, 140.6 mmol) and bis(trimethylsilyl)malonate (38.0 mL, 147.7 mmol) with Et3N (41 mL, 295.4 mmol) and LiBr (13.5 g, 154.7 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (24.8 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as an orange solid (5.6 g).

Sources & evidence

ORD record
ord-32d8d277e8c847da9ce802614118df1a
Source dataset
uspto-grants-2006_03
Patent number
US07018998B2

Reaction notes

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