反応 #57478

反応方程式

di-tert-butyl azodicarboxylate

cyclohexanol

N-hydroxypthalimide

di-tert-butyl azodicarboxylate

→

2-(cyclohexyloxy)-1H-isoindole-1,3(2H)-dione

収率 75.1%

溶媒

tetrahydrofuran

tetrahydrofuran

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added to the reaction mixture
2. 2
   その他After evaporation in vacuo
3. 3
   workup.ADDITIONthe residue was treated with trifluoroacetic acid (100 mL)
4. 4
   workup.STIRRINGstirred for 20 minutes
5. 5
   その他The reaction was evaporated in vacuo
6. 6
   その他the residue was partitioned between water and dichloromethane
7. 7
   その他The layers were separated
8. 8
   抽出the aqueous phase was extracted with dichloromethane
9. 9
   乾燥The combined organic layers were dried over anhydrous magnesium sulfate
10. 10
    ろ過filtered
11. 11
    その他evaporated in vacuo to a residue
12. 12
    その他The crude material was purified twice by flash silica gel chromatography
13. 13
    洗浄eluting with hexane:ethyl acetate (4:1 and 9:1)
14. 14
    濃縮Pure fractions were concentrated in vacuo to a solid
15. 15
    その他dried under high vacuum

実験手順

A solution of triphenylphosine (15.53 g, 59.2 mmol), cyclohexanol (6.25 mL, 59.2 mmol), and N-hydroxypthalimide (9.66 g, 59.2 mmol) in anhydrous tetrahydrofuran (500 mL) under Argon was treated dropwise over approximately 20 minutes with a solution of di-tert-butyl azodicarboxylate (15.00 g, 65.14 mmol) in tetrahydrofuran (100 mL) with a water bath to control the exotherm. After the reddish color had dissipated, a mixture of di-tert-butyl azodicarboxylate (3.00 g, 13.0 mmol) and triphenylphosine (3.11 g, 11.8 mmol) in anhydrous tetrahydrofuran (50 mL) was added to the reaction mixture and allowed to stir overnight at ambient temperature. After evaporation in vacuo, the residue was treated with trifluoroacetic acid (100 mL) and stirred for 20 minutes. The reaction was evaporated in vacuo and the residue was partitioned between water and dichloromethane. The layers were separated and the aqueous phase was extracted with dichloromethane. The combined organic layers were dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to a residue. The crude material was purified twice by flash silica gel chromatography eluting with hexane:ethyl acetate (4:1 and 9:1). Pure fractions were concentrated in vacuo to a solid and dried under high vacuum to provide 2-(cyclohexyloxy)-1H-isoindole-1,3(2H)-dione as a solid (10.90 g, 75%).

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