Methanol → N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine

HRID 1618806ノート

反応式

HRID 1618806 の反応式
[O:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH2:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:27])[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([CH:25]=O)[C:18]=2[O:17]1.CO.[BH4-].[Na+]>C(O)=O>[CH3:15][C:16]1([CH3:27])[CH2:20][C:19]2[CH:21]=[CH:22][CH:23]=[C:24]([CH2:25][NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[O:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:18]=2[O:17]1

参加物

6

反応物 4

HCID 887MethanolHCID 75899Benzenamine, 2-phenoxy-HCID 27954712,2-Dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehydeHCID 4311764Sodium borohydride

生成物 1

HCID 67257445N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine収率 86%

試薬・触媒・溶媒 1

HCID 284Formic Acid溶媒

反応条件

温度
90 °C

実験手順

A mixture of 2-phenoxy-phenylamine (350 mg, 1.89 mmol) and 2,2-dimethyl-2,3-dihydro-1-benzofuran-7-carbaldehyde (500 mg, 2.83 mmol) was heated at 90° C. for 2 h under nitrogen. The reaction was cooled to 0° C. and MeOH (4 mL) was added, followed by NaBH4 (216 mg, 5.70 mmol) in portions over 20 min. The mixture was stirred at room temperature for 24 h. Formic acid (0.4 mL was added and the mixture stirred for 15 min. The solvents were removed in vacuo, the residue quenched with saturated aqueous NaHCO3 (50 mL), extracted with DCM (2×30 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with petroleum spirit (A) and ethyl acetate (B) (5-10% B, 80 g, 3 CV, 60 mL/min) to afford 560 mg (86%) of N-(2,2,-Dimethyl-2,3-dihydrobenzofuran-7-ylmethyl)-N-(2-phenoxy phenyl)amine as a colourless oil.

後処理

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringthe mixture stirred for 15 min
  3. customThe solvents were removed in vacuo
  4. customthe residue quenched with saturated aqueous NaHCO3 (50 mL)
  5. extractionextracted with DCM (2×30 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customsolvents removed in vacuo
  9. customThe crude material was purified by silica gel chromatography
  10. washeluting with petroleum spirit (A) and ethyl acetate (B) (5-10% B, 80 g, 3 CV, 60 mL/min)

出典と根拠

ORDレコード
ord-a8ebcc8e0fee4352a7749861bb429eec
出典データセット
uspto-grants-2014_07
特許番号
US08771641B2

反応ノート

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