反应详情

To a solution of 400 g (3.44 mol) of valeric acid hydrazide (Lancaster Synthesis) in 3000 mL of dichloromethane under a nitrogen atmosphere, was added 250 g (2 mol) of anhydrous magnesium sulfate and 310 g (3.88 mol) of butyraldehyde. The reaction was stirred at ambient temperature for 17 h, filtered, and concentrated in vacuo providing 613 g of nearly colorless solid: mp 66.5-68.0° C.; NMR (CDCl3) δ 0.97 (t, J=7 Hz, 3H), 0.92 (t, J=7 Hz, 3H), 1.31-1.46 (m, 2H), 1.48-1.73 (m, 4H), 2.19-2.28 (m, 2H), 2.62 (t, J=7 Hz, 2H), 7.14 (t, J=6 Hz, 1H), 9.18 (br s, 1H). This material was dissolved in 3000 mL of ethanol and cooled to 0° C. in an ice bath prior to the addition of 130.1 g (3.44 mol) of sodium borohydride. The reaction was maintained at 0° C. for 3 h and then allowed to slowly warm to ambient temperature overnight. The volatiles were removed in vacuo and the residue dissolved in 1500 mL of water and continuously extracted with ether/dichloromethane (1:1) overnight. The extracts were dried (Na2SO4) and concentrated in vacuo to give 549 g (93%) of colorless N2 -butyl valeric acid hydrazide: mp 66.0-67.5° C.; NMR (CDCl3) δ 0.92 (t, J=7 Hz, 6H), 1.17-1.52 (m, 6H), 1.56-1.69 (m, 2H), 2.14 (t, J=7 Hz, 2H), 2.82 (t, J=7 Hz, 2H).

1. filtrationfiltered
2. concentrationconcentrated in vacuo
3. customproviding 613 g of nearly colorless solid
4. temperaturecooled to 0° C. in an ice bath
5. temperatureThe reaction was maintained at 0° C. for 3 h
6. temperatureto slowly warm to ambient temperature overnight
7. customThe volatiles were removed in vacuo
8. dissolutionthe residue dissolved in 1500 mL of water
9. extractioncontinuously extracted with ether/dichloromethane (1:1) overnight
10. dry with materialThe extracts were dried (Na2SO4)
11. concentrationconcentrated in vacuo