Acetic Anhydride → Acetic acid 1-methyl-1-(2-methyl-pyridin-3-yl)-ethyl ester

HRID 1592397Notes

Reaction equation

[CH3:1][C:2]1[C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:12][C:13](OC(C)=O)=[O:14]>CN(C1C=CN=CC=1)C>[CH3:10][C:8]([O:11][C:13](=[O:14])[CH3:12])([C:7]1[C:2]([CH3:1])=[N:3][CH:4]=[CH:5][CH:6]=1)[CH3:9]

Participants

Conditions

Temperature: 100 °C

Procedure

2-(2-methyl-pyridin-3-yl)-propan-2-ol (1.30 g, 8.61 mmol) and DMAP (30 mg) were combined in Ac2O (8 mL) and stirred at 100° C. for 16 hours. Following removal of the solvent under reduced pressure, the brown residue was quenched with saturated NaHCO3 (50 mL) and extracted with CH2Cl2 (5×60 mL). The combined organic extracts were dried (Na2SO4), filtered, and concentrated in vacuo to afford a yellow oil. Purification via column chromatography on silica gel (CH2Cl2:MeOH, 95:5, v/v) afforded acetic acid 1-methyl-1-(2-methyl-pyridin-3-yl)-ethyl ester as a white crystalline solid (1.25 g, 75%). 1H NMR (CDCl3) δ 1.80 (s, 3H), 2.05 (s, 3H), 2.66 (s, 3H), 7.12 (dd, 1H, J=9.0, 6.0 Hz), 7.62 (dd, 1H, J=9.0, 3.0 Hz), 8.39 (dd, 1H, J=6.0, 3.0 Hz).

Workup

customremoval of the solvent under reduced pressure
customthe brown residue was quenched with saturated NaHCO3 (50 mL)
extractionextracted with CH2Cl2 (5×60 mL)
dry with materialThe combined organic extracts were dried (Na2SO4)
filtrationfiltered
concentrationconcentrated in vacuo
customto afford a yellow oil
customPurification via column chromatography on silica gel (CH2Cl2

Sources & evidence

ORD record: ord-d00dd014feb44710b58516897a39f1b9
Source dataset: uspto-grants-2007_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07291631B2

Reaction notes

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