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. The mixture was stirred at 0° C. for 48 h. The reaction 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, the residue was separated on SiO2 (70 g) (CHCl3-MeOH 0 to 10%). Colorless oil, 9.83 g (0.057 mol, 93%). 1H NMR (300 MHz, DMSO) δ 7.20-7.40 (m, 4H), 5.39 (d, J=4.6 Hz, 1H), 4.76 (t, J=5.8 Hz, 1H), 4.54 (q, 4.9=Hz, 1H), 3.43 (m, 2H)

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 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-f525b16602464a2daa097247a86862dc

出典データセット

uspto-grants-2014_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08629147B2