تفاعل #164460

معادلة التفاعل

azide

azide

triflic azide

azide

Azide

ninhydrin

NaBH4

BF3

OEt2

→

4-(2-azidoethyl)-benzyl alcohol

المردود 82.0%

المذيبات

THF

THF

ظروف التفاعل

المعالجة

1. 1
   أخرىat 0° C
2. 2
   workup.STIRRINGThe mixture was stirred at room temperature for 14 h
3. 3
   workup.STIRRINGstirring
4. 4
   workup.WAITcontinued for about 18 h
5. 5
   أخرىExcess boron trifluoride etherate was destroyed with ethanol
6. 6
   ترشيحthe mixture filtered
7. 7
   أخرىThe filtrate was evaporated
8. 8
   أخرىto afford a semi solid
9. 9
   أخرىThe crude was purified on silica gel eluting with EtOAc/Hexanes 2:3

الإجراء التجريبي

To a solution of this carboxylic acid (0.70 g, 3.87 mmol) in anhydrous THF (8 mL) was added 1M BH3:THF (12 mL, 12.0 mmol) at 0° C. Stirring was continued at 0° C. for 1 h and the reaction was warmed up to room temperature. The mixture was stirred at room temperature for 14 h. TLC (visualization with ninhydrin stain) showed azide reduction took place. NaBH4 (0.46 g, 12 mmol) and BF3:OEt2 (1.6 mL, 12 mmol) were added and stirring continued for about 18 h to ensure a complete azide reduction. Excess boron trifluoride etherate was destroyed with ethanol, and the mixture filtered. The filtrate was evaporated to afford a semi solid. The crude was treated with freshly prepared triflic azide (12 mmol) as described for the synthesis of azide 14s. The crude was purified on silica gel eluting with EtOAc/Hexanes 2:3 to afford 4-(2-azidoethyl)-benzyl alcohol as clear oil (0.56 g, 82%) (Rf=0.53, EtOAc/Hexanes 2:3).

المصدر