反応 #166179

反応方程式

DIAD

(S)-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol

N-hydroxyphthalimide

triphenylphosphine

→

crude title compound

2-[(S)-2-(tert-Butyl-dimethyl-silanyloxy)-propoxy]isoindole-1,3-dione

溶媒

THF

反応条件

後処理

1. 1
   workup.ADDITIONDuring the addition the reagents
2. 2
   workup.DISSOLUTIONdissolved
3. 3
   workup.ADDITIONbefore fading to pale yellow colour on completion of the addition
4. 4
   濃縮The reaction mixture was concentrated in vacuo
5. 5
   workup.DISSOLUTIONthe resultant residue re-dissolved in diethyl ether
6. 6
   ろ過The suspension was filtered
7. 7
   濃縮the filtrate was concentrated in vacuo

実験手順

To a suspension of (S)-2-(tert-butyl-dimethyl-silanyloxy)-propan-1-ol (53.0 g, 0.28 mol), N-hydroxyphthalimide (47.0 g, 0.29 mol) and triphenylphosphine (77.9 g, 0.30 mol) in THF (200 ml) at 0° C. was added dropwise DIAD (56.8 ml, 0.29 mol). During the addition the reagents dissolved and the solution turned a dark red colour before fading to pale yellow colour on completion of the addition. The reaction mixture was stirred and allowed to warm to room temperature overnight. The reaction mixture was concentrated in vacuo and the resultant residue re-dissolved in diethyl ether. The suspension was filtered and the filtrate was concentrated in vacuo to yield the crude title compound as a pale yellow oil. The material was used without further purification in the subsequent step.

出典