Acetic Acid → (1-Benzofuran-2-ylmethyl)(methyl)amine

HRID 18299

反応式

HRID 18299 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[CH:10]=O.CN.CC(O)=O.[BH3-][C:19]#[N:20].[Na+]>CO>[CH3:19][NH:20][CH2:10][C:2]1[O:1][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=1

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6329MethylamineHCID 613412-BenzofurancarboxaldehydeHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 5048607(1-Benzofuran-2-ylmethyl)(methyl)amine収率 50.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a stirred solution of 2-benzofurancarboxaldehyde (2.22 g, 15.2 mmole) in MeOH (5 mL) was added 2 M methylamine in MeOH (15 mL), HOAc (0.86 mL, 15 mmole), and NaBH3CN (1.0 g, 15.9 mmole). The reaction was stirred for 18 h at RT then concentrated under vacuum. The remaining residue was taken up in Et2O, and the solution was washed with 1 N NaOH then brine, dried (Na2SO4), and concentrated to dryness. Purification by flash chromatography on silica gel (5% (5% NH4OH in MeOH)/CHCl3) gave the title compound (1.23 g, 50%) as a pale yellow oil: MS (ES) m/e 162.4 (M+H)+.

後処理

  1. concentrationthen concentrated under vacuum
  2. washthe solution was washed with 1 N NaOH
  3. dry with materialbrine, dried (Na2SO4)
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography on silica gel (5% (5% NH4OH in MeOH)/CHCl3)

出典と根拠

ORDレコード
ord-d7310d87c3a64ad6a5110a3cb477819a
出典データセット
uspto-grants-2010_06
特許番号
US07741339B2

関連ノート

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