Dimethyl Sulfoxide → 3-(4-Methoxyphenyl)propanal

Temperature

-78 °C

A solution of dimethyl sulfoxide (5.1 mL) in dichloromethane (10 ml) was added to a stirred solution of oxalyl chloride (3.0 mL, 36 mmol) in dichloromethane (40 ml) at −78° C. over 30 min. Upon completion of the addition, the mixture was stirred at −78° C. for 5 min, followed by addition of a solution of 4-methoxybenzenepropanol (3.0 g, 18 mmol) in dichloromethane (20 ml) at −78° C. over 30 min. The resulting mixture was stirred at −78° C. for 40 min. Next, triethylamine (15 mL, 110 mmol) was added dropwise over 10 min. The resulting mixture was allowed to warm to 0° C. and stirred at this temperature for 1 hour. It was diluted with dichloromethane (30 mL) and quenched with water (15 mL). The organic extracts were separated, washed with water and brine, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with ethyl acetate in hexanes (gradient: 3 min: 0/100 to 23 min: 20/80) to afford the desired product (1.50 g, 51%).

1. additionUpon completion of the addition
2. stirringThe resulting mixture was stirred at −78° C. for 40 min
3. temperatureto warm to 0° C.
4. stirringstirred at this temperature for 1 hour
5. customquenched with water (15 mL)
6. customThe organic extracts were separated
7. washwashed with water and brine
8. dry with materialdried over magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated under reduced pressure
11. customThe residue was purified by flash chromatography
12. washeluting with ethyl acetate in hexanes (gradient: 3 min: 0/100 to 23 min: 20/80)

ORD record

ord-5f5260d3c483476db72abc4c3936ad64

Source dataset

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07767675B2