Reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=[O:8])([O-:3])=[O:2].C(N(CC)CC)C.[CH3:19][O:20][P:21]([O-:24])[O:22][CH3:23]>C(OCC)(=O)C>[CH3:19][O:20][P:21]([CH:7]([OH:8])[C:6]1[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)(=[O:24])[O:22][CH3:23]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
3-Nitrobenzaldehyde (20 g, 0.132 mol) was dissolved in 100 mL of ethyl acetate. Triethylamine (22 mL, 0.158 mol, 1.2 eq) was added, followed by dimethylphosphite (15.7 mL, 0.171 mmol, 1.3 eq) and the mixture was stirred at room temperature. After 2 hours the mixture was diluted with 150 mL of ethyl acetate and washed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was treated with ethyl ether to obtain a beige solid, which was filtered and dried under vacuum at 40° C. for 1 h (26.7 g, 77% yield).
Workup
- washwashed with saturated aqueous ammonium chloride (2×50 mL) and water (50 mL)
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure
- additionThe residue was treated with ethyl ether
- customto obtain a beige solid, which
- filtrationwas filtered
- customdried under vacuum at 40° C. for 1 h (26.7 g, 77% yield)
Sources & evidence
- ORD record
- ord-6b6d0775abb64f6ba1883c5aa00c22cb
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541575B2
Linked notes
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