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

HRID 859366Notes

Reaction equation

HRID 859366 reaction equation
[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](Cl)=[O:8].C[Si]([C:14]([Si](C)(C)C)([C:18]([O-:20])=[O:19])[C:15]([O-:17])=[O:16])(C)C.CCN([CH2:30][CH3:31])CC.[Li+].[Br-].OS(O)(=O)=O.[CH3:39]C#N>C(OC(C)=C)(=O)C>[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7](=[O:8])[CH2:14][C:15]([OH:17])=[O:16].[Cl:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]1[O:8][C:30]([CH3:31])([CH3:39])[O:20][C:18](=[O:19])[CH:14]=1

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8471TriethylamineHCID 82050Lithium BromideHCID 27358243-Chlorothiophene-2-carbonyl chlorideHCID 222245802,2-Bis(trimethylsilyl)propanedioate

Product 2

HCID 222246163-(3-Chloro-thiophen-2-yl)-3-oxo-propionic acidHCID 222247756-(3-Chloro-thiophen-2-yl)-2,2-dimethyl-[1,3]dioxin-4-one

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

The 3-(3-chloro-thiophen-2-yl)-3-oxo-propionic acid was prepared from 3-chloro-thiophene-2-carbonyl chloride (7.82 g, 43.2 mmol) and bis(trimethylsilyl)malonate (11.6 mL, 45.4 mmol) with Et3N (12.65 mL, 90.7 mmol) and LiBr (3.53 g, 47.5 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (5.69 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 (2.3 g).

Sources & evidence

ORD record
ord-53e1892dc84943f4a75f9dfcf7a3e118
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

Loading…