4-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-ol → 4-(4-Chloro-2-methoxy-phenyl)-butan-1-ol

HRID 2383997ノート

反応式

HRID 2383997 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][CH2:10][CH2:11][OH:12])=[C:4]([O:13][CH3:14])[CH:3]=1.[H][H]>C(OCC)(=O)C.O=[Pt]=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][CH2:11][OH:12])=[C:4]([O:13][CH3:14])[CH:3]=1

参加物

5

反応物 2

HCID 591924974-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-olHCID 178418361HCID 178418361、化合物2 回

生成物 1

HCID 591925024-(4-Chloro-2-methoxy-phenyl)-butan-1-ol収率 89.7%

試薬・触媒・溶媒 2

HCID 345198Adams' catalyst触媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of 4-(4-chloro-2-methoxy-phenyl)-but-3-yn-1-ol (2.2 g, 10.4 mmol) and PtO2 (200 mg) in ethyl acetate (15 mL) was hydrogenated under 50 psi hydrogen atmosphere until no more hydrogen uptake was observed. The reaction mixture was then filtered and concentrated in vacuo. The crude product was subjected to column chromatography on silica gel (gradient elution with 0%-40% EtOAc/hexane) to give 4-(4-chloro-2-methoxy-phenyl)-butan-1-ol as a colorless oil (2 g, 89.7%). 1H NMR (300 MHz, CDCl3) δ ppm 7.03 (d, J=8.2 Hz, 1H), 6.86 (dd, J=8.2, 1.6 Hz, 1H), 6.81 (d, J=1.6 Hz, 1H), 3.81 (s, 3H), 3.66 (t, J=6.0 Hz, 2H), 2.49-2.65 (m, 2H), 1.50-1.72 (m, 5H).

後処理

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-b475b7532ae24b95b3497a364b11bc14
出典データセット
uspto-grants-2012_09
特許番号
US08263656B2

反応ノート

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