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

HRID 636743ノート

反応式

HRID 636743 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-780071aa4aef4ec6ac9f65041a14ea17
出典データセット
uspto-grants-2001_02
特許番号
US06194461B1

反応ノート

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