3-Bromo-2,5-dimethoxybenzaldehyde → 3-Bromo-2,5-dimethoxybenzyl Alcohol

HRID 1835994

反応式

HRID 1835994 の反応式
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[CH:5]=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([CH2:5][OH:6])[CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1

参加物

4

反応物 2

HCID 9310963-Bromo-2,5-dimethoxybenzaldehydeHCID 21226445Aluminium lithium hydride

生成物 1

HCID 101927773-Bromo-2,5-dimethoxybenzyl Alcohol収率 93%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a cooled (0° C.) solution of 51 (8.0 g, 33 mmol) in THF (100 ml) was added LiAlH4 (15 ml of 1.0M in THF) dropwise. After 15 min, the reaction was quenched with 2N HCl and the aqueous layer was extracted with EtOAc. The EtOAc layer was dried concentrated to give a solid (7.5 g, 93%): Mp=65-67° C.; 1H NMR (DMSO-d6) δ 7.05 (d, 1 H, J=3.0 Hz), 6.98 (d, 1 H, J=2.5 Hz), 5.28 (t, 1 H, J=4.9 Hz), 4.47 (d, 2 H, J=5.7 Hz), 3.73 (s, 3 H), 3.67 (s, 3 H); MS 245 (M−H)−

後処理

  1. customthe reaction was quenched with 2N HCl
  2. extractionthe aqueous layer was extracted with EtOAc
  3. dry with materialThe EtOAc layer was dried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-f03923f1153f4479855097c93705d95a
出典データセット
uspto-grants-2004_08
特許番号
US06774248B2

関連ノート

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