Acetic Anhydride → HCID 67272412, compound

HRID 250978Notes

Reaction equation

[CH:1]1([C:7]2[C:8]([CH3:14])=[N+:9]([O-])[CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:15][C:16]([O:18]C(C)=O)=[O:17]>>[CH:1]1([C:7]2[C:8]([CH2:14][O:18][C:16](=[O:17])[CH3:15])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 672726033-cyclohexyl-2-methylpyridine N-oxide

Product 1

HCID 67272412HCID 67272412, compound

Conditions

Temperature: 90 °C

Procedure

The N-oxide from above (0.215 g) was dissolved in Ac2O (2.5 mL) and heated to 90° C. for 24 h followed by removal of the solvent under reduced pressure. The crude material was purified by column chromatography (50:1 CH2Cl2/MeOH) to give the rearranged acetic acid 3-cyclohexyl-pyridin-2-ylmethyl ester as a light brown solid (0.23 g, 99%, 2 steps). 1H NMR (CDCl3) δ 1.25-1.45 (m, 5H), 1.78-1.86 (m, 5H), 2.13 (s, 3H), 2.70 (m, 1H), 7.24 (m, 1H), 7.62 (d, 1H, J=6.0 Hz), 8.46 (d, 1H, J=2.8 Hz).

Workup

customfollowed by removal of the solvent under reduced pressure
customThe crude material was purified by column chromatography (50:1 CH2Cl2/MeOH)

Sources & evidence

ORD record: ord-1d6e3504587d4fb5a878ba965221d2fa
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863293B2

Reaction notes

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