반응 #71144

반응 방정식

2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carboxylic acid ethyl ester

DiBAL

N2

→

title compound

[2-(tert-Butyl-dimethyl-silanyloxymethyl)-oxazol-4-yl]-methanol

용매

THF

toluene

EA

Rochelle's salt

반응 조건

후처리

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGthe mixture stirred at rt for 2 h
3. 3
   기타The layers were separated
4. 4
   추출the aq. layer extracted with EA (3×20 mL)
5. 5
   건조extracts were dried over Na2SO4
6. 6
   여과filtered
7. 7
   기타the solvents were removed under reduced pressure

실험 절차

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 2-(tert-butyl-dimethyl-silanyloxymethyl)-oxazole-4-carboxylic acid ethyl ester (830 mg, 2.91 mmol) in THF (15.0 mL) was treated at 0° C. with DiBAL (11.6 mL of a 1M sol in toluene, 11.60 mmol) and the reaction mixture was stirred for 45 min at 0° C. The reaction mixture was then diluted with EA (5.0 mL), sat. aq. Rochelle's salt (20.0 mL) was added and the mixture stirred at rt for 2 h. The layers were separated and the aq. layer extracted with EA (3×20 mL). The combined org. extracts were dried over Na2SO4, filtered, and the solvents were removed under reduced pressure to give the title compound as a yellow solid. TLC: rf (EA)=0.59. LC-MS-conditions 02: tR=0.94 min; [M+H]+=244.46.

출처