Hexane → 6-[2-n-Butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5yl]-4-hexenoic acid

Temperatur

0 °C

To a suspension of (4-carboxybutyl)triphenyl-phosphonium bromide (1.04 g, 2.35 mmol) in dry tetrahydrofuran (25 mL) at 0° C. under argon was added n-butyl lithium in hexane (1.8 mL of 2.5M, 4.6 mmol). The reaction mixture was stirred for 15 minutes at 0° C. and then a solution of 2-n-butyl-1-(2-chlorophenyl)methyl-1H-imidazol-5-carboxaldehyde [Example 6 (iii)] (0.5 g, 1.81 mmol) in tetrahydrofuran (25 mL) was added dropwise. The mixture was stirred an additional hour at 0° C. and then at ambient temperature for 3 days. Water was added and the mixture was extracted with diethyl ether. The aqueous layer was acidified to pH 3 with aqueous hydrochloric acid solution. The product was extracted into ethyl acetate, washed with water, dried, concentrated, and chromatographed over silica gel eluting with 5-10% methanol in methylene chloride to give 0.24 g of 6-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-4-hexenoic acid.

1. stirringThe mixture was stirred an additional hour at 0° C.
2. waitat ambient temperature for 3 days
3. extractionthe mixture was extracted with diethyl ether
4. extractionThe product was extracted into ethyl acetate
5. washwashed with water
6. customdried
7. concentrationconcentrated
8. customchromatographed over silica gel eluting with 5-10% methanol in methylene chloride

ORD-Eintrag

ord-f292aa281dd543869c402cc2b082136b

Quelldatensatz

uspto-grants-1996_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05530017