反応 #343413

反応方程式

dimethylformamide

product

6-bromo-hexahydro-3,5-methano-2-H-cyclopenta[b]furan-2-ol

p-toluene sulfonic acid

dimethylformamide

→

(S)α-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene-acetonitrile

溶媒

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   温度the mixture was refluxed for another 15 minutes
2. 2
   その他returned to room temperature
3. 3
   洗浄The mixture was washed with water
4. 4
   その他dried
5. 5
   ろ過vacuum filtered
6. 6
   その他evaporated to dryness under reduced pressure
7. 7
   その他The 4.34 g of the (R,S)α-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene acetonitrile were chromatographed over silica gel
8. 8
   洗浄eluted with a 9-1 hexane-ethyl acetate mixture
9. 9
   その他to obtain the (S)α-isomer melting at 65° C.

実験手順

A solution of 2.19 g of the product of Step B in 50 ml of methylene chloride was added to a refluxing mixture of 2.93 g of (R,S)α-cyano-3-phenoxy-benzyl alcohol, 100 ml of methylene chloride and 300 mg of p-toluene sulfonic acid and the mixture was refluxed for another 15 minutes and then returned to room temperature. The mixture was washed with water, dried, vacuum filtered and evaporated to dryness under reduced pressure. The 4.34 g of the (R,S)α-[(2S)(6-bromo-hexahydro-3,5-methano-2H-cyclopenta[b]furan-2-yl)-oxy]-3-phenoxy-benzene acetonitrile were chromatographed over silica gel and eluted with a 9-1 hexane-ethyl acetate mixture to obtain the (S)α-isomer melting at 65° C. and having a specific rotation of [α]D20 =+110° (c=0.5% in dimethylformamide) and the (R)α-isomer with a specific rotation of [α]D20 =+108.5° (c=0.4% in dimethylformamide).

出典