Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 15392027, compound

HRID 343546Notes

Reaction equation

HRID 343546 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:20][CH2:19][C:18]4(OCC[O:21]4)[CH2:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([C:25]#[C:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=4)[CH2:16][CH2:17][C:18](=[O:21])[CH2:19][CH2:20]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 153920264-(3-Cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-pyridylethynyl)cyclohexane

Product 1

HCID 15392027HCID 15392027, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(3-cyclopentyloxy-4-methoxyphenyl)-1,1-(ethylenedioxy)-4-(2-pyridylethynyl)cyclohexane (0.17 g, 0.39 mmol) and pyridinium p-toluenesulfonate (0.10 g, 0.39 mmol) in acetone (4 mL) and water (1 mL) was refluxed for three days, then was evaporated. Water was added, the mixture was extracted three times with dichloromethane, the extract was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 25:75 ethyl acetate:hexanes, provided 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-(2-pyridylethynyl)cyclohexan-1-one as a wax. 1H-NMR (400 MHz, CDCl3) δ 8.61 (d, J=4.8 Hz, 1H), 7.68 (dt, J=7.8, 1.8 Hz, 1H), 7.47 (d, J=7.8 Hz, 1H), 7.27 (m, 1H), 7.20 (d, J=2.3 Hz, 1H), 7.15 (dd, J=8.5, 2.4 Hz, 1H), 6.87 (d, J=8.5 Hz, 1H), 4.81 (m, 1H), 3.85 (s, 3H), 3.07 (dt, J=14.4, 5.8 Hz, 2H), 2.49 (d, J=14.8 Hz, 2H), 2.41 (m, 2H), 2.27 (dt, J=13.4, 3.9 Hz, 2H), 1.8-2.0 (m, 6H), 1.61 (m, 2H). Anal. (C25H27NO3.0.65 H2O) calcd: C, 74.84; H, 7.11; N, 3.49; found: C, 75.00; H, 6.83; N, 3.52.

Workup

  1. temperaturewas refluxed for three days
  2. customwas evaporated
  3. additionWater was added
  4. extractionthe mixture was extracted three times with dichloromethane
  5. dry with materialthe extract was dried (magnesium sulfate)
  6. customwas evaporated
  7. customPurification by flash chromatography
  8. washeluting with 25:75 ethyl acetate

Sources & evidence

ORD record
ord-afdfe794fad046e9b31eb74672b620d1
Source dataset
uspto-grants-1999_01
Patent number
US05861421

Reaction notes

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