反应详情

To a solution of (R or S)-3-cyanocyclohex-3-en-1-yl propanoate (210 g, 1.17 mol) in 1:1 THF/EtOH (2 L) at 0° C. was added 3M aqueous NaOH (586 mL, 1.76 mol) dropwise via addition funnel over 30 minutes. After addition, The mixture was stirred at ambient temperature for 2 hours. The mixture was carefully neutralized with 3N aqueous HCl (195 mL), concentrated to remove most of the THF/EtOH. The resulting mixture was diluted with brine (1.5 L) and extracted with EtOAc (1.2 L, then 600 mL×4). The combined organics were washed with brine (200 mL×2). The aqueous layer was back-extracted with EtOAc (200 mL×2), and the combined organic extracts were dried over anhydrous Na2SO4, and concentrated in vacuo to give the enantioenriched title compound (chiral HPLC: 98.4% ee). 1H NMR data was consistent with that reported in the literature for racemic 5-Hydroxycyclohex-1-enecarbonitrile.

1. additiondropwise via addition funnel over 30 minutes
2. additionAfter addition
3. concentrationconcentrated
4. customto remove most of the THF/EtOH
5. additionThe resulting mixture was diluted with brine (1.5 L)
6. extractionextracted with EtOAc (1.2 L
7. washThe combined organics were washed with brine (200 mL×2)
8. extractionThe aqueous layer was back-extracted with EtOAc (200 mL×2)
9. dry with materialthe combined organic extracts were dried over anhydrous Na2SO4
10. concentrationconcentrated in vacuo