반응 #48005

반응 방정식

(trimethylsilyl)diazomethane

(Trimethylsilyl)diazomethane

2-(2-hydroxymethylindan-2-yl)-isoindole-1,3-dione

fluoroboric acid

water

→

2-(2-methoxymethylindan-2-yl)-isoindole-1,3-dione

용매

CH2Cl2

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction is stirred for a further 40 minutes after the final
2. 2
   workup.ADDITIONaddition
3. 3
   추출extracted with dichloromethane
4. 4
   세척The organic phase is washed with brine
5. 5
   건조dried (MgSO4)
6. 6
   기타evaporated
7. 7
   기타The crude product is purified by flash chromatography (CH2Cl2 elution)

실험 절차

(Trimethylsilyl)diazomethane (2 M hexanes, 0.51 ml, 1.03 mmol) is added dropwise to a cooled (0° C.) solution of 2-(2-hydroxymethylindan-2-yl)-isoindole-1,3-dione (0.150 g, 0.511 mmol) and fluoroboric acid (48% aqueous, 93.5 μl, 0.511 mmol) in CH2Cl2 (4 ml). The reaction is stirred for 20 minutes, then three further portions of (trimethylsilyl)diazomethane (2 M hexanes, 0.128 ml, 0.25 mmol; 64 μl, 0.12 mol; 64 μl, 0.12 mmol)) are made at 20 minute intervals. The reaction is stirred for a further 40 minutes after the final addition, poured into water and extracted with dichloromethane. The organic phase is washed with brine, dried (MgSO4) and evaporated. The crude product is purified by flash chromatography (CH2Cl2 elution) to afford 2-(2-methoxymethylindan-2-yl)-isoindole-1,3-dione, MH+308.

출처