Acetic Anhydride → 2-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)butyl acetate

HRID 1195666Notes

Reaction equation

HRID 1195666 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][C:14]([CH2:25][CH3:26])([CH2:23][CH3:24])[CH:15]([C:17]2[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=2)[OH:16])=[CH:11][CH:10]=1>N1C=CC=CC=1>[C:1]([O:16][CH:15]([C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[C:14]([CH2:13][C:12]1[CH:11]=[CH:10][C:9]([Cl:8])=[CH:28][CH:27]=1)([CH2:23][CH3:24])[CH2:25][CH3:26])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 151008322-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol

Product 1

HCID 541723282-(4-Chlorobenzyl)-2-ethyl-1-(3-pyridyl)butyl acetate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

10.2 g (0.10 mol) of acetic anhydride are added dropwise to a solution of 12.1 g (0.04 mol) of 2-(4chlorobenzyl)-2-ethyl-1-(3-pyridyl)-1-butanol in 50 ml of pyridine at room temperature, and the mixture is then heated at 80° C. for 8 h. The reaction mixture is concentrated, the residue is taken up in 200 ml of dichloromethane, and the solution is washed with saturated NaHCO3 solution and then with water. The organic phase is dried and concentrated, and the remaining black oil is purified on silica gel (mobile phase: 5:1 cyclohexane/ethyl acetate). 11.2 g (81% of theory) of the title compound are obtained as a viscous yellow oil.

Workup

  1. concentrationThe reaction mixture is concentrated
  2. washthe solution is washed with saturated NaHCO3 solution
  3. customThe organic phase is dried
  4. concentrationconcentrated
  5. customthe remaining black oil is purified on silica gel (mobile phase: 5:1 cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-63e97ab3d7c24574a8504429d13e52dc
Source dataset
uspto-grants-1992_05
Patent number
US05112828

Reaction notes

Loading…