Methylamine → (3-Ethyl-benzofuran-2-ylmethyl)methylamine

HRID 1362314ノート

反応式

HRID 1362314 の反応式
[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH:12]=O)[CH3:2].[CH3:14][NH2:15].[BH4-].[Na+]>CO>[CH2:1]([C:3]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[O:5][C:4]=1[CH2:12][NH:15][CH3:14])[CH3:2]

参加物

5

反応物 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 126115243-Ethyl-1-benzofuran-2-carbaldehyde

生成物 1

HCID 59277558(3-Ethyl-benzofuran-2-ylmethyl)methylamine収率 89%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

3-Ethyl-benzofuran-2-carbaldehyde (1.16 g, 6.65 mmol) was added to a solution of methylamine (26 mL of a 2M solution in MeOH, 52 mmol) and the resulting mixture was stirred overnight. The mixture was concentrated under reduced pressure. The residue was taken up in ethanol (20 mL) and then cooled in an ice-bath. NaBH4 (370 mg, 9.90 mmol) was added in one portion. The mixture was concentrated under reduced pressure and the residue taken up in 1 M NaOH. The mixture was extracted with Et2O (3×). The combined organics were washed with brine, dried and concentrated under reduced pressure to give the title compound (1.12 g, 89%) as a yellow oil: 1H NMR (300 MHz, DMSO-d6) δ 7.58 (dd, J=8.4, 6.6 Hz, 1H), 7.46 (d, J=7.2 Hz, 1H), 7.30-7.25 (m, 2H), 3.75 (s, 2H), 2.68 (t, J=7.5 Hz, 2H), 2.26 (s, 3H), 2.05 (br s, 1H), 1.21 (t, J=7.5 Hz, 3H); ESI MS m/z 190 (M+H)+.

後処理

  1. concentrationThe mixture was concentrated under reduced pressure
  2. temperaturecooled in an ice-bath
  3. concentrationThe mixture was concentrated under reduced pressure
  4. extractionThe mixture was extracted with Et2O (3×)
  5. washThe combined organics were washed with brine
  6. customdried
  7. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-8d447af8520143179e5731acef24be77
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

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