반응 #1064412

반응 방정식

THF

1,3-diphenylpropanone

tetrahydrofuran

(+)-B-chlorodiisopinocampheyl-borane

→

(1R)-1,3-diphenyl-1-propanol

수율 61.0%

반응 조건

후처리

1. 1
   workup.ADDITIONtreated with
2. 2
   기타After evaporating to dryness
3. 3
   workup.ADDITIONthe residue was treated with ether (65 mL) and diethanolamine (1.0 g)
4. 4
   여과The mixture was then filtered
5. 5
   기타to remove solids
6. 6
   농축concentrated
7. 7
   기타the residue was purified
8. 8
   세척gradient elution (5% ethyl acetate/hexane to 10% ethyl acetate) on a silica gel column

실험 절차

A solution of 1,3-diphenylpropanone (1.07 g; 5.09 mmol) in tetrahydrofuran (10 mL) was cooled to -23° C. and treated with an asymmetric reducing agent, (+)-B-chlorodiisopinocampheyl-borane (1.80 g; 5.60 mmol) in 20 mL THF, and the resulting solution was allowed to stand overnight at -23° C. After evaporating to dryness, the residue was treated with ether (65 mL) and diethanolamine (1.0 g) and stirred for 3 hrs. The mixture was then filtered to remove solids and concentrated, and the residue was purified using gradient elution (5% ethyl acetate/hexane to 10% ethyl acetate) on a silica gel column to obtain 660 mg (61%) of (1R)-1,3-diphenyl-1-propanol as a crystalline white solid, 1H NMR (360 Mhz; CDCl3): d 1.95-2.15 (m, 3H); 2.59-2.78 (m, 2H); 4.65 (dd, 1H, J=5.4, 7.8); 7.14-7.35 (m, 10H).

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