반응 #1381664

반응 방정식

sodium hydrogencarbonate

(R)-4-hydroxy4-hydroxymethyl-6-chloro-8-difluoromethoxychromane

water

→

sub-title compound

수율 71.5%

(R)-4-Hydroxy-6-chloro-8-difluoromethoxychroman-4-yl carboxylic acid

수율 71.5%

용매

acetone

반응 조건

후처리

1. 1
   기타A stream of air was bubbled through the solution
2. 2
   여과The solution was filtered through Celite
3. 3
   세척the filter-cake was washed with water
4. 4
   추출saturated with NaCl and extracted with EtOAc (3×)
5. 5
   세척The combined ethyl acetate phases were washed with water (2×) and with brine
6. 6
   건조dried (Na2SO4)
7. 7
   농축concentrated
8. 8
   workup.DISSOLUTIONThe residue was dissolved in ether
9. 9
   세척The ether solution was washed with water (3×)
10. 10
    농축concentrated

실험 절차

To a solution of (S)- or (R)-4-hydroxy4-hydroxymethyl-6-chloro-8-difluoromethoxychromane (3.2 g, 11.4 mmol, from step (vii) above) in acetone (25 mL) was added non-ionized water (110 mL), then sodium hydrogencarbonate (2.13 g, 22.2 mmol) and Pt/C 5%, 58% water (2.13 g). A stream of air was bubbled through the solution with stirring at 75° C. (oil-bath) overnight. The solution was filtered through Celite and the filter-cake was washed with water. The acetone-water solution was acidified (HCl, 2M) to pH 2, saturated with NaCl and extracted with EtOAc (3×). The combined ethyl acetate phases were washed with water (2×) and with brine, then dried (Na2SO4) and concentrated. The residue was dissolved in ether. The ether solution was washed with water (3×) and concentrated, yielding 2.4 g (71%) of the sub-title compound.

출처