Hydrochloric Acid → 2-(Thiophen-3-yl)propanal

A solution of methoxymethyldiphenyl phosphonium chloride (4 g, 11.9 mmol) in anhydrous ethanol (50 ml) was cooled to 0° C. and sodium ethoxide (0.8 g, 8.25 mmol) was added. After the mixture had warmed to room temperature, 1-thiophen-3-yl-ethanone (0.7 g, 5.9 mmol) was added and the reaction mixture was heated to 120° C. for 30 min in Microwave. The mixture was filtered and the filtrate was concentrated. The crude product was purified by silica gel column chromatograph using EtOAc:Hexane/20:80 as the eluent to give 0.5 g (54.5% yield) 3-((E or Z)-2-methoxy-1-methyl-vinyl)-thiophene. The solution of 3-((E or Z)-2-methoxy-1-methyl-vinyl)-thiophene in THF:HCl: H2O (10 ml total, 9:0.5:1) was heated to 150° C. for 30 min in microwave. After the mixture was concentrated the residue was partitioned between EtOAc and water. The combined organic layers were washed with sodium bicarbonate, water, brine, dried over sodium sulfate and concentrated to give the title compound as an oil 250 mg (30%).

1. concentrationAfter the mixture was concentrated the residue
2. customwas partitioned between EtOAc and water
3. washThe combined organic layers were washed with sodium bicarbonate, water, brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated

ORD record

ord-824c8b03be5f428a9c6b40304b97e3ff

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07365085B2