반응 #40763

반응 방정식

2-(2-Methyl-[1,3]dioxolan-2-yl)-butyric acid ethyl ester

LiAlH4

→

2-(2-Methyl-[1,3]dioxolan-2-yl)-butan-1-ol

용매

Et2O

Et2O

반응 조건

후처리

1. 1
   온도cooled in an ice bath
2. 2
   온도The mixture was refluxed for 4 h.
3. 3
   온도cooled in an ice bath
4. 4
   기타quenched
5. 5
   workup.ADDITIONby adding H2O (16.1 mL), 2M aqueous NaOH (32.2 mL) and again H2O (16.1 mL)
6. 6
   여과The suspension was filtered
7. 7
   세척the filter cake was washed with Et2O
8. 8
   기타the combined filtrates were evaporated to dryness
9. 9
   workup.DISTILLATIONThe residue (49 g) was purified by vacuum distillation (112-125° C., 15 mbar)
10. 10
    기타yielding 43.5 g of a clear, colorless liquid

실험 절차

2-(2-Methyl-[1,3]dioxolan-2-yl)-butyric acid ethyl ester (85.5 g) was taken up in dry Et2O (50 mL). This mixture was added dropwise to a suspension of LiAlH4 (16.1 g) in dry Et2O (200 mL), cooled in an ice bath. The mixture was refluxed for 4 h., cooled in an ice bath, and quenched by adding H2O (16.1 mL), 2M aqueous NaOH (32.2 mL) and again H2O (16.1 mL). The suspension was filtered, the filter cake was washed with Et2O, and the combined filtrates were evaporated to dryness. The residue (49 g) was purified by vacuum distillation (112-125° C., 15 mbar), yielding 43.5 g of a clear, colorless liquid. 1H NMR (400 MHz, CDCl3) δ 0.98 (t, J=7.5 Hz, 3H), 1.10-1.24 (m, 1H), 1.31 (s, 3H), 1.50-1.75 (m, 2H), 3.12, (br s, 1H), 3.59-3.76 (m, 2H), 3.94-4.02 (m, 4H).

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