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

HRID 2383997Notes

Reaction equation

HRID 2383997 reaction equation
[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

Participants

5

Reactant 2

HCID 591924974-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-olHCID 178418361HCID 178418361, compound2×

Product 1

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

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b475b7532ae24b95b3497a364b11bc14
Source dataset
uspto-grants-2012_09
Patent number
US08263656B2

Reaction notes

Loading…