反応 #155405

反応方程式

N-Boc-3-azetidinone

2-tert-butoxy-2-oxoethyl-zinc chloride

Et2O

→

tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate

溶媒

THF

反応条件

後処理

1. 1
   その他The reaction was then quenched with sat. aq. NH4Cl (10 mL)
2. 2
   その他the aqueous layer was separated
3. 3
   抽出extracted with ethyl acetate (2×30 mL)
4. 4
   洗浄The combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL)
5. 5
   乾燥dried over Na2SO4
6. 6
   ろ過filtered
7. 7
   濃縮concentrated to dryness

実験手順

To a stirring solution of N-Boc-3-azetidinone (0.45 g, 2.64 mmol) in THF (5 mL) was slowly added a 0.5 M solution of 2-tert-butoxy-2-oxoethyl-zinc chloride in Et2O (10 mL, 5.0 mmol), and the reaction mixture was stirred for 5 h. The reaction was then quenched with sat. aq. NH4Cl (10 mL), and the aqueous layer was separated and extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with 5% aq. NaHCO3 (2×10 mL), brine (15 mL), dried over Na2SO4, filtered and concentrated to dryness to yield tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate (MS m/e [M+H]+ calcd 288.2. found 287.7).

出典