Water → HCID 19434628, compound
Reaction equation
O.[CH2:2]([NH2:6])[CH2:3][CH2:4][CH3:5].[C:7](OCC)(=[O:10])[C:8]#[CH:9].[Na+].[Cl-]>C(O)(=O)C>[CH2:2]([NH:6][C:7](=[O:10])[C:8]#[CH:9])[CH2:3][CH2:4][CH3:5]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 30 mL of water and 7.68 g (105 mmol) n-Butylamine is added dropwise 9.8 g (100 mmol) ethyl propiolate at 0° C. for 30 minutes. The mixture was stirred for 2 h at 0° C., then acetic acid (2 mL) was added. The mixture was stirred for another 10 minutes and saturated with NaCl, followed by extraction with ethyl acetate (3×20 mL). The combined organic phase was washed with saturated aqueous solution of NaHCO3 (20 mL), dried over Na2SO4, and removed by rotary evaporation to give product (12.0 g, yield 95%, purity 69% by GC).
Workup
- extractionfollowed by extraction with ethyl acetate (3×20 mL)
- washThe combined organic phase was washed with saturated aqueous solution of NaHCO3 (20 mL)
- dry with materialdried over Na2SO4
- customremoved by rotary evaporation
- customto give product (12.0 g, yield 95%, purity 69% by GC)
Sources & evidence
- ORD record
- ord-74f37a7def2e4109854eed6bc93d4eb7
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08895780B2
Reaction notes
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