Dimethyl Sulfoxide → Cyclopentanepropanal

Temperatur

-78 °C

To CH2Cl2 (100 mL) at −78° C. were added oxalyl chloride (4.1 mL, 46.8 mmol, Aldrich) and dry DMSO (5.5 mL, 78.0 mmol, Aldrich), dropwise. After 5 min, 3-cyclopentylpropan-1-ol (5.0 g, 39.0 mmol, Aldrich) in 5 mL of CH2Cl2 was added. The mixture was stirred for an additional 0.5 hr at −78° C., and triethylamine (27.2 mL, 195.0 mmol) was added. The mixture was then allowed to warm to room temperature over 0.5 hr. After stirring for 3 hr, 100 mL of water was added. The phases were separated, and the aqueous phase was extracted with diethyl ether (3×100 mL). The combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl. The organic layer was dried (MgSO4), filtered and concentrated to provide 4.1 g (83%) of the title compound. MS (ESI+) m/z 144 (M+NH4)+.

1. temperatureto warm to room temperature over 0.5 hr
2. stirringAfter stirring for 3 hr
3. customThe phases were separated
4. extractionthe aqueous phase was extracted with diethyl ether (3×100 mL)
5. washThe combined organic extracts were washed successively with 50 mL of aqueous 1% HCl, 50 mL of water, 50 mL of aqueous 5% NaHCO3 and 50 mL of saturated aqueous NaCl
6. dry with materialThe organic layer was dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD-Eintrag

ord-edc7e3228bfc4186afdab44c06df5b99

Quelldatensatz

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08835475B2