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

HRID 2383997노트

반응식

HRID 2383997 반응식
[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

참가 물질

5

반응물 2

HCID 591924974-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-olHCID 178418361HCID 178418361, 화합물2회

생성물 1

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

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-b475b7532ae24b95b3497a364b11bc14
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263656B2

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