Water → HCID 59339357, compound
Reaction equation
O.[NH2:2][NH2:3].[CH:4](=[C:11]([CH2:14][CH3:15])[CH:12]=O)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.O>CCOCC>[CH2:14]([CH:11]1[CH:4]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)[NH:3][N:2]=[CH:12]1)[CH3:15]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
62 ml (10 equiv.) hydrazine hydrate was added to 150 mL diethylether. The emulsion was cooled with an ice/NaCl bath to −10° C. A solution of 20.4 g 2-benzylidene-butyraldehyde in 100 mL ether was added dropwise at −10° C. and stirred at −10° C. for 3 hours. The mixture was stirred overnight (with ice bath) and allowed to slowly reach room temperature H2O was added, the organic layer was separated and the aqueous layer was extracted 2 times with diethylether. The combined organic layers were dried over Na2SO4, filtrated and concentrated in vacuo. Vacuum destination yielded 6.1 g of a clear fluid (102-106° C., 0.6 mbar) containing 94% of the desired product (mixture of diastereomeric pairs). Characteristic signals of the first diastereomeric pair: 1H NMR (400 MHz, CDCl3) δ 0.83 (t, J=6.5 Hz, 3H), 3.03-3.13 (m, 1H), 4.74-4.81 (m, 1H), 6.83 (br s, 1H). Characteristic signals of the second diastereomeric pair: 1H NMR (400 MHz, CDCl3) δ 1.00 (t, J=7.5 Hz, 3H), 2.84-2.93 (m, 1H), 4.28-4.34 (m, 1H), 6.76 (br s, 1H).
Workup
- stirringThe mixture was stirred overnight (with ice bath)
- additionwas added
- customthe organic layer was separated
- extractionthe aqueous layer was extracted 2 times with diethylether
- dry with materialThe combined organic layers were dried over Na2SO4
- filtrationfiltrated
- concentrationconcentrated in vacuo
- customVacuum destination yielded 6.1 g of a clear fluid (102-106° C., 0.6 mbar)
Sources & evidence
- ORD record
- ord-6b9c95a31ad94f898252eaa163b5a2a7
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07728018B2
Reaction notes
Loading…