Dimethylformamide → (Diphenyl-phosphinoyl)-acetaldehyde

HRID 1920893ノート

反応式

HRID 1920893 の反応式
[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]=1

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 75041Phosphine oxide, diphenylmethyl-HCID 178418339Butyllithium

生成物 1

HCID 11042963(Diphenyl-phosphinoyl)-acetaldehyde

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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]+.

後処理

  1. customAfter 2 h at −78° C. the mixture was quenched with HCl (1 N, 25 mL)
  2. temperaturethe resulting mixture warmed up to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined organic layers were then washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated

出典と根拠

ORDレコード
ord-13b6df294d5e44e9bb9c4391d6a2dc23
出典データセット
uspto-grants-2012_05
特許番号
US08173652B2

反応ノート

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