Ammonium Chloride → 2-Tetradecylsulfanyl-ethanol

Temperature

0 °C

A solution of tetradecylsulfanyl-acetic acid (1.50 g, 520 mmol) in dry THF (10 ml) was added drop wise to a suspension of LiAlH4 (0.40 g, 10.4 mmol) in dry THF (30 ml) at 0° C. The mixture was stirred at 0° C. for one hour and then at ambient temperature for 18 hours. Saturated NH4Cl (40 ml) was added, and the resulting mixture was filtered through a short pad of celite. The phases were separated and the aqueous layer was extracted with diethyl ether (50 ml). The combined organic phases was washed with brine (50 ml), dried (Na2SO4) and concentrated in vacuo. Purification by flash chromatography on silica gel (heptane:EtOAc 4:1) afforded 0.76 g (54%) of the title compound as a colourless solid.

1. waitat ambient temperature for 18 hours
2. filtrationthe resulting mixture was filtered through a short pad of celite
3. customThe phases were separated
4. extractionthe aqueous layer was extracted with diethyl ether (50 ml)
5. washThe combined organic phases was washed with brine (50 ml)
6. dry with materialdried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customPurification by flash chromatography on silica gel (heptane:EtOAc 4:1)

ORD record

ord-df8d6bd600174234ba0e525241dfa679

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741966B2