反応 #342074

反応方程式

Borane dimethylsulfide

compound 1

7-benzyloxy-3-(4-methoxyphenyl)-2H-1-benzopyran

THF

THF

→

title compound 4

収率 60.0%

chroman-4-ol

収率 60.0%

反応条件

後処理

1. 1
   その他After completion of the reaction
2. 2
   その他the mixture was quenched with H2O (7 mL)
3. 3
   workup.ADDITIONfollowed by addition of 10% NaOH (2 mL) and 37% H2O2 (0.36 mL)
4. 4
   workup.STIRRINGAfter stirring for 30 min
5. 5
   抽出the mixture was extracted with CH2Cl2 (30 mL×5)
6. 6
   乾燥dried with anhydrous MgSO4
7. 7
   ろ過After filtration
8. 8
   濃縮the filtrate was concentrated in vacuo
9. 9
   その他followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4)

実験手順

Borane-dimethylsulfide complex (BH3—SMe2) (10 M, 1.14 mL, 11.4 mmol) in THF was added dropwise at 0° C. to a solution of compound 1 (1 g, 2.9 mmol) in THF (12 mL), and the resultant mixture was stirred at 0° C. for 4 hrs. After completion of the reaction, the mixture was quenched with H2O (7 mL), and then continually stirred for 5 min, followed by addition of 10% NaOH (2 mL) and 37% H2O2 (0.36 mL). After stirring for 30 min, the mixture was extracted with CH2Cl2 (30 mL×5). The organic layers were combined and dried with anhydrous MgSO4. After filtration, the filtrate was concentrated in vacuo, followed by purification via silica gel column chromatography (ethyl acetate/n-hexane=1:4), thus giving the title compound 4 as a colorless crystal (0.63 g, 60% yield).

出典