Dimethyl Sulfoxide → HCID 75586866, compound

Temperature

-78 °C

Oxalyl chloride (580 mg, 392 μL, 4.6 mmol) was diluted in CH2Cl2 (12 mL) under argon and the solution was cooled to −78° C. Dry DMSO (715 mg, 650 μL, 9.15 mmol) in CH2Cl2 (3 mL) was added to the cold solution dropwise and the mixture was stirred for 30 min. A solution of alcohol 23 (500 mg, 1.83 mmol) in CH2Cl2 (4 mL) was then added slowly, and the mixture was kept stirring for an additional hour at −78° C. Et3N (1.3 g, 1.8 mL, 12.8 mmol) was then introduced, the white suspension was stirred at −78° C. for 20 min and slowly warmed to rt. A 0.5 M phosphate buffer solution pH 5.5 (20 mL) was added, the two phases were separated and the resulting aqueous phase was extracted with Et2O (4×). The combined organic phase was dried (MgSO4), filtered, and evaporated. The residue was purified by flash column chromatography using hexanes/EtOAc (6:1 to 4:1) to yield the desired aldehyde 24 (433 mg, 86%) as a light yellow oil. TLC: Rf=0.76 (hexanes/EtOAc=1:1); 1H NMR (CDCl3, 300 MHz) δ 9.77 (t, J=1.3 Hz, 1H), 4.35 (m, 1H), 4.30-4.19 (m, 3H), 4.04 (dd, J=2.3, 9.8 Hz, 1H), 3.92 (ddd, J=5.3, 6.7, 9.5 Hz, 1H), 3.77 (dd, J=1.7, 10.1 Hz, 1H), 3.75 (ddd, J=5.2, 6.2, 9.5 Hz, 1H), 2.69 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 200.1, 88.3, 76.1, 71.8, 63.1, 43.7, 23.3.

1. stirringthe mixture was kept stirring for an additional hour at −78° C
2. stirringthe white suspension was stirred at −78° C. for 20 min
3. temperatureslowly warmed to rt
4. customthe two phases were separated
5. extractionthe resulting aqueous phase was extracted with Et2O (4×)
6. dry with materialThe combined organic phase was dried (MgSO4)
7. filtrationfiltered
8. customevaporated
9. customThe residue was purified by flash column chromatography

ORD record

ord-524d2f7dc238422d958932f2f1cc270c

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09024038B2