Water → (S)-1-(3-Chlorophenyl)ethane-1,2-diol

AD mix alpha (86.0 g) was added to a stirred mixture of tert-BuOH (300 mL) and H2O (300 mL), mixture was stirred for 15 min at RT, than cooled to 0° C. 3-Chlorostyrene (8.51 g, 0.061 mol) was added over 15 min and the mixture was stirred at 0° C. for 48 h. The reaction mixture was quenched by adding 10% aq. sodium sulfite (120 mL) followed by addition of EtOAc (200 mL). The layers were separated and the aqueous layer was extracted with EtOAc (200 mL). The combined organic layers were washed with 0.4 M H2SO4 in saturated Na2SO4 (100 mL), followed by drying over Na2SO4. The solvent was evaporated and the residue was separated on SiO2 (70 g) (CHCl3-MeOH 0 to 10%). Colorless oil, 9.83 g (0.057 mol, 93%).

1. additionAD mix alpha (86.0 g)
2. temperaturethan cooled to 0° C
3. stirringthe mixture was stirred at 0° C. for 48 h
4. customThe reaction mixture was quenched
5. additionby adding 10% aq. sodium sulfite (120 mL)
6. additionfollowed by addition of EtOAc (200 mL)
7. customThe layers were separated
8. extractionthe aqueous layer was extracted with EtOAc (200 mL)
9. washThe combined organic layers were washed with 0.4 M H2SO4 in saturated Na2SO4 (100 mL)
10. dry with materialby drying over Na2SO4
11. customThe solvent was evaporated
12. customthe residue was separated on SiO2 (70 g) (CHCl3-MeOH 0 to 10%)

ORDレコード

ord-3249624626664111b8737c2ccf80536c

出典データセット

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08063225B2