反应详情

(S)-6-chloro-3-phenylindan-1-one (IVa) (isolated as in example 7) (23 g) is added in small portions to a suspension of sodium borohydride (1.6 g) in ethanol (160 ml) at 3-5° C. After the addition has been finalised, the mixture is allowed to reach room temperature. The reaction mixture is stirred for 2.75 hours, where after it is evaporated to dryness. The residue is dissolved in a mixture of water (150 ml) and ethyl acetate (200 ml), the phases are separated, and the water phase is extracted with ethyl acetate (100 ml). The organic phases are combined, washed with water (100 ml), dried with magnesium sulphate, filtered and evaporated to dryness. The residue is recrystallised from heptanes (250 ml), giving 20.9 g (90%) of the title product as a solid. Melting point 108.9° C., NMR conforms to structure, [α]D20 +48.30° (c=1.0, methanol). CHN calculated for C15H13OCl: C, 73.62; H, 5.35; found: C, 73.55; H, 5.29. >99% ee according to the chiral analysis.

1. additionAfter the addition
2. customto reach room temperature
3. customwhere after it is evaporated to dryness
4. dissolutionThe residue is dissolved in a mixture of water (150 ml) and ethyl acetate (200 ml)
5. customthe phases are separated
6. extractionthe water phase is extracted with ethyl acetate (100 ml)
7. washwashed with water (100 ml)
8. dry with materialdried with magnesium sulphate
9. filtrationfiltered
10. customevaporated to dryness
11. customThe residue is recrystallised from heptanes (250 ml)