반응 #710554

반응 방정식

tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-fluoroallylcarbamate

TBAF

→

(E)-tert-butyl 3-fluoro-2-(hydroxymethyl)allylcarbamate

수율 15.6%

(Z)-tert-butyl 3-fluoro-2-(hydroxymethyl)-allylcarbamate

수율 6.5%

용매

THF

반응 조건

후처리

1. 1
   workup.WAITThe resulting solution was left
2. 2
   기타The reaction mixture was partitioned between water (70 mL) and ethyl acetate (50 mL)
3. 3
   추출The aqueous layer was extracted with ethyl acetate (50 mL)
4. 4
   세척the combined organics were washed with saturated aqueous NH4Cl (70 mL)
5. 5
   건조After drying over Na2SO4
6. 6
   농축the organics were concentrated in vacuo
7. 7
   기타Purification of the crude material over silica gel eluting with 20% ethyl acetate and 5% THF in n-hexane

실험 절차

To a stirring solution of tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-fluoroallylcarbamate (E/Z=1:1; 12.0 g, 37.6 mmol) in THF (30 mL) at room temperature was added TBAF (1:0 M in THF; 45.1 mL, 45.1 mmol). The resulting solution was left to stir for 30 min. The reaction mixture was partitioned between water (70 mL) and ethyl acetate (50 mL). The aqueous layer was extracted with ethyl acetate (50 mL) and the combined organics were washed with saturated aqueous NH4Cl (70 mL) followed by brine (70 mL). After drying over Na2SO4, the organics were concentrated in vacuo. Purification of the crude material over silica gel eluting with 20% ethyl acetate and 5% THF in n-hexane gave (Z)-tert-butyl 3-fluoro-2-(hydroxymethyl)-allylcarbamate (0.5 g, 6.5%), (E)-tert-butyl 3-fluoro-2-(hydroxymethyl)allylcarbamate (1.2 g, 15.6%) and a mixture of the E/Z isomers (5.5 g, 71.4%).

출처