Dimethylformamide → (Diphenyl-phosphinoyl)-acetaldehyde
Reaction equation
[CH3:1][P:2](=[O:15])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[Li]CCCC.CN([CH:24]=[O:25])C>C1COCC1>[C:3]1([P:2]([CH2:1][CH:24]=[O:25])([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[O:15])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -78 °C
Procedure
To a solution of methyldiphenylphosphine oxide (2.0 g, 9.0 mmol) in THF (60 mL) at 0° C. was added BuLi (1.6 M in hexane, 6.94 mL, 11.0 mmol) and after 2 h at 0° C., the mixture was cooled to −78° C. and then DMF (0.85 mL, 11 mmol) was added. After 2 h at −78° C. the mixture was quenched with HCl (1 N, 25 mL) and the resulting mixture warmed up to room temperature. The mixture was extracted with ethyl acetate and the combined organic layers were then washed with water and brine and then dried over sodium sulfate, filtered and evaporated. The crude product (off-white oil, 2.41 g) was used directly in the next step. MS: m/e=245.2 [M+H]+.
Workup
- customAfter 2 h at −78° C. the mixture was quenched with HCl (1 N, 25 mL)
- temperaturethe resulting mixture warmed up to room temperature
- extractionThe mixture was extracted with ethyl acetate
- washthe combined organic layers were then washed with water and brine
- dry with materialdried over sodium sulfate
- filtrationfiltered
- customevaporated
Sources & evidence
- ORD record
- ord-13b6df294d5e44e9bb9c4391d6a2dc23
- Source dataset
- uspto-grants-2012_05
- Patent number
- US08173652B2
Reaction notes
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