Dimethylformamide → (S)-1-butyloxy-2-hydroxypropane

Temperature

70 °C

(S)-1-hydroxy-2-tetrahydropyranyloxypropane (120 g, 0.75 mol) was dropwise added to sodium hydride (44.8 g, 1.87 mol) in THF (400 ml), followed by adding DMF (200 ml), agitating the mixture for 2 hours, dropwise adding to the mixture, butyl bromide (112.4 g, 0.82 mol) at 30° C. or lower, agitating the mixture at room temperature for 6 hours, adding toluene, sufficiently agitating the mixture, washing the resulting organic layer with 2N-NaOH aqueous solution and then with water, drying it over anhydrous magnesium sulfate, distilling off toluene, adding to the resulting oily residue, pyridium p-toluenesulfonate (18 g) and ethanol (500 ml), heating the mixture at 70° C. for one hour, distilling off ethanol, adding toluene to the residue, sufficiently washing the mixture with water, distilling off toluene and distilling the residue to obtain (S)-1-butyloxy-2-hydroxypropane (79.3 g) (b.p. 87° C./35 mmHg) (αD24 =+3.6 (l=1.0 dm neat)).

1. stirringlower, agitating the mixture at room temperature for 6 hours
2. stirringsufficiently agitating the mixture
3. washwashing the resulting organic layer with 2N-NaOH aqueous solution
4. dry with materialwith water, drying it over anhydrous magnesium sulfate
5. distillationdistilling off toluene
6. additionadding to the resulting oily residue, pyridium p-toluenesulfonate (18 g) and ethanol (500 ml)
7. distillationdistilling off ethanol
8. additionadding toluene to the residue
9. washsufficiently washing the mixture with water
10. distillationdistilling off toluene
11. distillationdistilling the residue

ORD record

ord-c7dc032282a44875b469337970f2cfe4

Source dataset

uspto-grants-1992_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05080827