Dimethylformamide → 1H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-

HRID 1268904노트

반응식

HRID 1268904 반응식
[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9](Br)=[CH:10][CH:11]=2)[CH2:6][CH2:5]1.[Li]CCCC.CN([CH:22]=[O:23])C>C1COCC1>[CH3:1][O:2][N:3]=[C:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:22]=[O:23])=[CH:10][CH:11]=2)[CH2:6][CH2:5]1

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 730128401H-Inden-1-one, 5-bromo-2,3-dihydro-, O-methyloximeHCID 178418339Butyllithium

생성물 1

HCID 730123441H-Indene-5-carboxaldehyde, 2,3-dihydro-1-(methoxyimino)-수율 65%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-60 °C

실험 절차

To a solution of the product of Step 1 (112 g, 0.46 mol) in THF (1500 ml) at −60° C. under argon, was added n-BuLi (325 ml, 0.52 mol) over 1 hour. After stirring at −60° C. for 1 hour a solution of DMF (39.7 ml) in THF (50 ml) was added dropwise over 1 hour. The reaction was stirred at −60° C. for 1 hour before being allowed to warm to room temperature. After 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted into ethyl acetate. The organic phase was then dried (Na2SO4), concentrated in vacuo and the residue purified by silica gel chromatography, to give the title compound (57 g, 65%) as a yellow solid; 1H NMR (CDCl3) 10.0 (1H, s), 7.83–7.73 (3H, m), 4.02 (3H, s), 3.10 (2H, m), 2.92 (2H, m).

후처리

  1. additionwas added dropwise over 1 hour
  2. temperatureto warm to room temperature
  3. customAfter 1 hour the reaction was quenched with saturated aqueous sodium hydrogen carbonate solution
  4. extractionextracted into ethyl acetate
  5. dry with materialThe organic phase was then dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-cd987730a5dd4ba183df1092dbed388f
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07199137B2

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