Acetic Acid → HCID 70043803, compound

To a solution of methyl (E)-3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-(2-thienyl)methyl-2-propenoate, prepared in Example 1, {(2.60 g. 6.06 mmol) in 35 mL of tetrahydrofuran at -78° C. under argon was added a solution of diisobutylaluminum hydride (1.5M, 8.9 mL, 13.3 mmol). After the addition was complete, the reaction mixture was allowed to warm to room temperature, with stirring being continued for one hour. The reaction was worked up by the slow addition of methanol, followed by the addition of glacial acetic acid, then four drops of 10% aqueous hydrochloric acid solution. Water (10 mL) was added and the reaction mixture was stirred at room temperature overnight. The product was extracted with ethyl acetate (3×75 mL) after 40 mL of water had been added to the mixture. The combined extracts were dried with anhydrous magnesium sulfate and the solvents were removed in vacuo. The residue was triturated with diethyl ether. The resulting solid was filtered to give 1.72 g (71%) of product; mp 114°-115° C.

1. additionAfter the addition
2. stirringthe reaction mixture was stirred at room temperature overnight
3. extractionThe product was extracted with ethyl acetate (3×75 mL) after 40 mL of water
4. additionhad been added to the mixture
5. dry with materialThe combined extracts were dried with anhydrous magnesium sulfate
6. customthe solvents were removed in vacuo
7. customThe residue was triturated with diethyl ether
8. filtrationThe resulting solid was filtered

ORD record

ord-c554c78ce7e6404687f49436b43babe2

Source dataset

uspto-grants-1993_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05185351