Ethyl Acetate → HCID 9899533, compound

HRID 902072Notes

Reaction equation

HRID 902072 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:7][C:6]([CH3:9])([CH3:8])[CH2:5][C:4]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)(O)[CH2:3]1.O=P(Cl)(Cl)Cl.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:19])[CH2:7][C:6]([CH3:8])([CH3:9])[CH2:5][C:4]([C:11]#[C:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:3]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 9921365HCID 9921365, compound

Product 1

HCID 9899533HCID 9899533, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3,3,5,5-Tetramethyl-1-(2-pyridinylethynyl)cyclohexanol (200 mg, 0.78 mmol) was dissolved in pyridine. POCl3 (153 mg, 1.0 mmol) was added, and the mixture was heated to reflux for 6 h. After cooling, the POCl3 and pyridine were removed in vacuo. The residue was purified by flash column chromatography on silica gel eluting with 2:1 hexane:ethyl acetate to afford 2-[(3,3,5,5-tetramethyl-1-cyclohexen-1-yl)-ethynyl]pyridine (148 mg, 80% yield) as a light tan solid. M.p. 55-56° C. 1H NMR (CDCl3, 300 MHz) Δ8.56 (m, 1H), 7.62 (m, 1H), 7.40 (d, J=7 Hz, 1H), 7.18 (m 1H), 6.09 (s, 1H), 2.00 (s, 2H), 1.35 (s, 2H), 1.05 (s, 6H), 0.99 (s, 6H).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. temperatureAfter cooling
  4. customthe POCl3 and pyridine were removed in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel eluting with 2:1 hexane

Sources & evidence

ORD record
ord-a6713d53df4549a99eb979aea59e7ef0
Source dataset
uspto-grants-2008_04
Patent number
US07365074B2

Reaction notes

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