Dimethyl Sulfoxide → HCID 178520943, Verbindung

Temperatur

-78 °C

To a solution of oxalyl chloride (6.2 mL, 87.4 mmol) in anhydrous CH2Cl2 (300 mL) was added dropwise DMSO (12.5 mL, 0.17 mol) at −78° C. under N2. After the mixture was stirred at −78° C. for 30 min., a solution of (trans-4-(trifluoromethyl)cyclohexyl)methanol (5.3 g, 29.1 mmol) in CH2Cl2 (40 mL) was added dropwise while keeping the internal temperature below −65° C. After being stirred for 30 min., a solution of Et3N (40.5 mL, 0.29 mol) in CH2Cl2 (60 mL) was added dropwise slowly, keeping the internal temperature below −65° C. The reaction mixture was stirred at −78° C. for 1 h, and warmed to rt overnight. The mixture was washed with water (3×300 mL) and brine (300 mL), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica (eluting with 15% EtOAc in petroleum ether) to give trans-4-(trifluoromethyl)cyclohexane-1-carbaldehyde (4.6 g, 87%) as a yellow oil.

1. customthe internal temperature below −65° C
2. stirringAfter being stirred for 30 min.
3. customthe internal temperature below −65° C
4. stirringThe reaction mixture was stirred at −78° C. for 1 h
5. temperaturewarmed to rt overnight
6. washThe mixture was washed with water (3×300 mL) and brine (300 mL)
7. dry with materialdried over anhydrous Na2SO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure
10. customThe residue was purified by column chromatography on silica (eluting with 15% EtOAc in petroleum ether)

ORD-Eintrag

ord-bf914da77a95471db7475a524d6ce070

Quelldatensatz

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09266886B2