Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 178444110, compound

HRID 254124Notes

Reaction equation

HRID 254124 reaction equation
C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[C:18]([CH:20]([C@H:34]1[CH2:39][CH2:38][C@H:37]([O:40][CH3:41])[CH2:36][CH2:35]1)[CH2:21][CH2:22][C:23]1(OCC[O:30]1)[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])#[N:19]>C(O)C.C(=O)(O)[O-].[Na+]>[C:18]([CH:20]([C@H:34]1[CH2:39][CH2:38][C@H:37]([O:40][CH3:41])[CH2:36][CH2:35]1)[CH2:21][CH2:22][C:23](=[O:30])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])#[N:19]

Participants

5

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 178442375HCID 178442375, compound

Product 1

HCID 178444110HCID 178444110, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Pyridinium p-toluenesulfonate (0.9 g, 3.6 mmol) was added to a solution of 1-cyano-1-(trans-4-methoxycyclohexyl)-4,4-(ethylenedioxy)decane (47) (6.2 g, 18.3 mmol) obtained in the first step dissolved in 120 mL of ethanol, and refluxed under heating for 10 hours. The reaction mixture was cooled to room temperature and then put in 100 mL of a saturated sodium bicarbonate aqueous solution, and then extracted with 100 mL of ethyl acetate. The resulting organic layer was washed with water (100 mL×2) and dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=9/1, column packing: silica gel) to obtain 1-cyano-1-(trans-4-methoxy cyclo hexyl)-4-decanone (48) (5.1 g, 17.4 mmol). The resulting compound was in the form of a colorless liquid, and the yield based on the compound (47) was 95%.

Workup

  1. customobtained in the first step
  2. temperaturerefluxed
  3. temperatureunder heating for 10 hours
  4. extractionextracted with 100 mL of ethyl acetate
  5. washThe resulting organic layer was washed with water (100 mL×2)
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by column chromatography (developing solvent: heptane/ethyl acetate=9/1, column packing: silica gel)

Sources & evidence

ORD record
ord-557aa1877e3f49918843e45c4cf10a75
Source dataset
uspto-grants-2011_01
Patent number
US07875327B2

Reaction notes

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