Dimethyl Sulfoxide → (2S)-2-(3,4-dichlorophenyl)pent-4-enal

Temperature

-78 °C

To a solution of oxalyl chloride (0.713 mL, 8.24 mmol) at −78° C. in dry methylene chloride (100 mL) under nitrogen in a three necked flask was added dropwise a solution of DMSO (1.37 mL, 19.8 mmol) in methylene chloride (4 mL) with stirring at −78° C. for an additional 20 min. A solution of (2S)-2-(3,4-dichlorophenyl)pent-4en-1-ol (1.26 g, 5.45 mmol) in methylene chloride (50 mL) was added dropwise (˜45 min) while maintaining the reaction temperature below −60° C. After stirring at −60° C. for an additional 2 h, triethylamine (4.6 mL, 33.3 mmol) was added dropwise. The stirred reaction mixture was allowed to warm to ambient temperature for 2 h, cooled in ice, quenched by addition of water (80 mL), and stirred for an additional 30 min. The organic layer was washed with water and brine, dried (Na2SO4), and evaporated to give 1.25 g of the title compound which was used without further purification. This material was determined to be about 72% pure by HPLC.

1. temperaturewhile maintaining the reaction temperature below −60° C
2. stirringAfter stirring at −60° C. for an additional 2 h
3. customThe stirred reaction mixture
4. temperatureto warm to ambient temperature for 2 h
5. temperaturecooled in ice
6. customquenched by addition of water (80 mL)
7. stirringstirred for an additional 30 min
8. washThe organic layer was washed with water and brine
9. dry with materialdried (Na2SO4)
10. customevaporated

ORD record

ord-e23179e83f3148b695bf7adab105f772

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235541B2