Dimethylformamide → (Diphenyl-phosphinoyl)-acetaldehyde

HRID 1920893노트

반응식

HRID 1920893 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 11042963(Diphenyl-phosphinoyl)-acetaldehyde

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-13b6df294d5e44e9bb9c4391d6a2dc23
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173652B2

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