Dimethyl Sulfoxide → (E)-3-(4-ethylphenyl)acrylaldehyde

General Procedure H. To a solution of oxalyl chloride (5.9 ml, 11.8 mmol, 2 M in CH2Cl2) in CH2Cl2 (20 ml) was added a solution of DMSO (1.1 ml, 15.7 mmol) in CH2Cl2 (3 ml) dropwise at −60° C. A solution of (E)-3-(4-ethylphenyl)prop-2-en-1-ol (Compound 40, 1.3 g, 7.8 mmol) in CH2Cl2 (5 ml) was cannulated slowly into the above mixture at −60° C. After the reaction was stirred at the same temperature for 1 hour, a solution of triethylamine (4.4 ml, 31.4 mmol) in CH2Cl2 (5 ml) was added into the reaction, which was stirred an additional 1 hour at −60° C. The reaction was quenched with water, and the products were extracted with CH2Cl2. The organic layer was washed with 5% aqueous NaHCO3, and brine, and dried over MgSO4. The filtered solution was concentrated in vacuo, and the residue was purified by column chromatography (silica gel, 15% ethyl acetate in hexane) to obtain the title compound as a clear oil.

1. customwas cannulated slowly into the above mixture at −60° C
2. stirringwas stirred an additional 1 hour at −60° C
3. customThe reaction was quenched with water
4. extractionthe products were extracted with CH2Cl2
5. washThe organic layer was washed with 5% aqueous NaHCO3, and brine
6. dry with materialdried over MgSO4
7. concentrationThe filtered solution was concentrated in vacuo
8. customthe residue was purified by column chromatography (silica gel, 15% ethyl acetate in hexane)

ORD record

ord-af09d11aafed42f59438f29d90dc1f26

Source dataset

uspto-grants-2010_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07728014B2