2,4-Difluorobenzaldehyde → n-(2,4-Difluorophenylmethyl)-n-[dimethyl(t-butyldimethylsiloxymethyl)methyl]amine

HRID 636743노트

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HRID 636743 반응식
[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH:4]=O.[O:11]([CH2:19][C:20]([NH2:23])([CH3:22])[CH3:21])[Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:3]=1[CH2:4][NH:23][C:20]([CH3:22])([CH3:21])[CH2:19][O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:13])[CH3:14]

참가 물질

4

반응물 2

HCID 737702,4-DifluorobenzaldehydeHCID 148067402-tert-Butyldimethylsilyloxy-1,1-dimethylethylamine

생성물 1

HCID 21255688n-(2,4-Difluorophenylmethyl)-n-[dimethyl(t-butyldimethylsiloxymethyl)methyl]amine수율 92%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

To a solution of 2,4-difluorobenzaldehyde (1.42 g, 10.0 mmol) in toluene (30 ml) was added 1-t-butyldimethylsiloxy-2-methyl-2-propylamine (2.03 g, 10.0 mmol) and stirred under reflux using a Dean-Stark trap to remove water for 6 hours. The solvent was evaporated and the residue was dissolved in methanol (10 ml). The solution was cooled to 0° C. in ice-water bath and an excess amount of NaBH4 was added. The mixture was gradually warmed to room temperature and stirring was continued until the Schiff base disappeared. The mixture was added to 1N NaOH aqueous solution, extracted with toluene, washed with sat. NaCl aqueous solution and dried over MgSO4. The solvent was evaporated to give the crude title compound (2.92 g; 92% in 2 steps).

후처리

  1. temperatureunder reflux
  2. customto remove water for 6 hours
  3. customThe solvent was evaporated
  4. dissolutionthe residue was dissolved in methanol (10 ml)
  5. additionan excess amount of NaBH4 was added
  6. temperatureThe mixture was gradually warmed to room temperature
  7. stirringstirring
  8. additionThe mixture was added to 1N NaOH aqueous solution
  9. extractionextracted with toluene
  10. washwashed with sat. NaCl aqueous solution
  11. dry with materialdried over MgSO4
  12. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-780071aa4aef4ec6ac9f65041a14ea17
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06194461B1

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