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

HRID 258262Notes

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

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-(4-chlorobenzyl)-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. 1H-NMR (CDCl3): δ=8.60(2-Hpy), 8.52(6-Hpy), 7.65(4-Hpy), 7.30(5-Hpy), 7.25(2Hm), 7.05(2Ho), 5.62(CHOAc), 2.68(CH2Ar), 2.08(COCH3), 1.45(CH2), 1.30(CH2), 0.95(CH3), 0.83(CH3).

Workup

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

Sources & evidence

ORD record: ord-69f217cc34c04da79fe324a223e57d35
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05266579

Reaction notes

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