Toluene → HCID 22841014, compound

A mixture of 1.037 g of dl-cis-2-benzyloxymethyl-3-hydroxytetrahydropyran (prepared as described in Preparation 9), 1.709 g of hexadecyl bromide, 0.77 g of potassium hydroxide and 15 ml of toluene was heated, with stirring, at 120° C. for 10 hours. The reaction mixture was cooled and then poured into water. The water layer was extracted twice with diethyl ether. The organic layer and the extracts were combined, washed with water, dried and condensed by evaporation under reduced pressure. The resulting oily residue, 3.3 g, was subjected to column chromatography through 50 g of silica gel. The fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane gave 1.455 g of the title compound as a colorless oily substance.

1. temperaturewas heated
2. temperatureThe reaction mixture was cooled
3. extractionThe water layer was extracted twice with diethyl ether
4. washwashed with water
5. customdried
6. customcondensed
7. customby evaporation under reduced pressure
8. washThe fraction eluted with a 1:10 by volume mixture of diethyl ether and hexane

ORD record

ord-06ca8ad9268c4c45a2f4b81c14c5ba6c

Source dataset

uspto-grants-1988_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04794183