Sulfuric Acid → HCID 14849727, compound

HRID 859375Notes

Reaction equation

HRID 859375 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].C[Si]([C:16]([Si](C)(C)C)([C:20]([O-:22])=[O:21])[C:17]([O-:19])=[O:18])(C)C.CCN([CH2:32][CH3:33])CC.[Li+].[Br-].OS(O)(=O)=O.[CH3:41]C#N>C(OC(C)=C)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:6](=[O:7])[CH2:16][C:17]([OH:19])=[O:18])[CH:9]=[CH:10][CH:11]=1.[CH3:41][C:32]1([CH3:33])[O:22][C:20](=[O:21])[CH:16]=[C:6]([C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:7]1

Participants

9

Reactant 6

HCID 1118Sulfuric AcidHCID 6342AcetonitrileHCID 8471TriethylamineHCID 74374m-Anisoyl chlorideHCID 82050Lithium BromideHCID 222245802,2-Bis(trimethylsilyl)propanedioate

Product 2

HCID 14849727HCID 14849727, compoundHCID 22224592HCID 22224592, compound

Reagents, catalysts & solvents 1

HCID 7916Isopropenyl acetateSolvent

Procedure

The 3-(3-methoxy-phenyl)-3-oxo-propionic acid was prepared from 3-methoxybenzoyl chloride (10.3 g, 60.4 mmol) and bis(trimethylsilyl)malonate (16.2 mL, 63.4 mmol) with Et3N (17.7 mL, 127 mmol) and LiBr (5.77 g, 66.4 mmol) in CH3CN at 0° C. according to general procedure H (method c1). The crude material (6.38 g) was transformed into the title compound by stirring in isopropenyl acetate and conc. H2SO4 according to general procedure J (method a). Obtained as a yellow oil (640 mg).

Sources & evidence

ORD record
ord-40244ca0e1a3492b998fc10fa66f6533
Source dataset
uspto-grants-2006_12
Patent number
US07151098B2

Reaction notes

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