Ethyl propiolate → 3-(Formylmethylhydrazono)-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:7])[C:5]#[CH:6])[CH3:2].[NH2:8][N:9]([CH3:12])C=O.[O:13]1CCOC[CH2:14]1>>[CH2:1]([O:3][C:4](=[O:7])[CH2:5][CH:6]=[N:8][NH:9][CH2:12][CH:14]=[O:13])[CH3:2]Participants
4
Procedure
39.24 g (0.4 mol) of propiolic acid ethyl ester were added to a solution of 29.63 g (0.4 mol) of N-amino-N-methylformamide in 80 ml of dioxane and left standing for 3 weeks at room temperature. The yellow solution was evaporated at 40° C./30 torr and the residue filtered over a silical gel column (350 g) with a mixture of dichloromethane/n-hexane 49:1 in fractions of 250 ml each. Fractions 2 to 10 were united and evaporated at 40° C./30 torr, yielding 63.9 g (93%) of 3-(formylmethylhydrazono)-propionic acid ethyl ester as a yellow fluid (IR: 3462, 2984, 1735, 1688, 1629, 1183, 1045 cm-1).
Workup
- waitleft
- waitstanding for 3 weeks at room temperature
- customThe yellow solution was evaporated at 40° C./30 torr
- filtrationthe residue filtered over a silical gel column (350 g) with a mixture of dichloromethane/n-hexane 49:1 in fractions of 250 ml each
- customevaporated at 40° C./30 torr
Sources & evidence
- ORD record
- ord-94b5991973554f4faa94aa2afc157177
- Source dataset
- uspto-grants-1999_04
- Patent number
- US05892040
Reaction notes
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