(S)-Oxiranemethanol

To 1.2 L of dichloromethane, 200 g of (S)-3-chloro-1,2-propanediol (99.5% ee) and 419 g of potassium phosphate were added. The resulting mixture was refluxed with stirring for 3 hours. The solution was then cooled to room temperature and filtered to remove the insoluble solid precipitate. The dichloromethane was then evaporated under reduced pressure. The residue was purified by fractional distillation (66°C/19 mmHg) to obtain 122 g of the target compound: (S)-glycidol. Yield: 122 g, Chemical purity: 99.0%, Optical purity (GC): 99.5%.

Figure (S) - Synthetic route of (S)-Oxiranemethanol

Colorless to light yellow liqui

Employed in the synthesis of chiral (E)-allylic alcohol side-chains for introduction into prostacyclin and prostaglandin frameworks by cross-metathesis.

ChEBI: (S)-glycidol is a glycidol. It is functionally related to a (S)-1,2-epoxypropane. It is an enantiomer of a (R)-glycidol.

Glycidol or 2,3-epoxy-1-propanol is a highly reactive epoxy derivative, which is generally used as a monomer in the preparation of many polymers like polyesters,polycarbonates,polyurethanes,and polyamides. It is also used in the preparation of detergents, rubbers, perfumes, fabric dyes, varnishes, cosmetics, and paints.

[S(-)-isomer, § also available on polymer support, has b 49-50o/7mm, 66-67o/19mm, [ ] D -1 5o(neat)], [R(+)-isomer has b 56 -5 6 . 5o/11mm, d 4 1.117, n D 1.429, [ ] D +15o (neat)]. Purify glycidol by fractional distillation.