Aluminium lithium hydride → 2-Propylamino-4-trifluoromethyl-benzaldehyde

HRID 1042446노트

반응식

HRID 1042446 반응식
CON(C)[C:4](=[O:19])[C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[NH:15][CH2:16][CH2:17][CH3:18].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH2:16]([NH:15][C:6]1[CH:7]=[C:8]([C:11]([F:12])([F:13])[F:14])[CH:9]=[CH:10][C:5]=1[CH:4]=[O:19])[CH2:17][CH3:18]

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86649954N-methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide

생성물 1

HCID 866499552-Propylamino-4-trifluoromethyl-benzaldehyde수율 99.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

N-Methoxy-N-methyl-2-propylamino-4-trifluoromethyl-benzamide (98.3 mg, 0.339 mmol) was reacted with 1M lithium aluminum hydride (0.6 ml) in THF (20 ml) at −40° C. for 1 hr. The reaction mixture was quenched by adding saturated potassium hydrogen sulfate solution. The mixture was stirred for 30 min. The reactions solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with CH2Cl2 (30 ml×3). The combined organic layer was dried over MgSO4 and concentrated in vacuo to yield 2-propylamino-4-trifluoromethyl-benzaldehyde (78 mg). 2-Propylamino-4-trifluoromethyl-benzaldehyde in toluene was reacted with methyl (triphenylphosphoranylidene) acetate (137 mg) at 100° C. overnight. The reaction solvent was removed in vacuo. Water (30 ml) was added to the resulting residue, which was extracted with ethyl acetate (30 ml×3). The combined organic layer was dried over MgSO4 and filtered. The filterate was concentrated in vacuo and purified with column chromatography to yield title compound (67 mg, 69%).

후처리

  1. customThe reaction mixture was quenched
  2. additionby adding saturated potassium hydrogen sulfate solution
  3. customThe reactions solvent was removed in vacuo
  4. additionWater (30 ml) was added to the resulting residue, which
  5. extractionwas extracted with CH2Cl2 (30 ml×3)
  6. dry with materialThe combined organic layer was dried over MgSO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4d8ad9c4774a413492c787a5c8b8484c
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08557872B2

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