Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 54132651, compound

HRID 726760Notes

Reaction equation

HRID 726760 reaction equation
C([O:3][CH:4](OCC)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C@H:12]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH:29]3[CH2:33][CH2:32][CH2:31][CH2:30]3)[CH:21]=2)[CH2:13][C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)=[CH:8][CH:7]=1)C.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CC(C)=O.O.CCOC(C)=O>[CH:29]1([O:28][C:22]2[CH:21]=[C:20]([C@@H:12]([C:9]3[CH:8]=[CH:7][C:6]([CH2:5][CH:4]=[O:3])=[CH:11][CH:10]=3)[CH2:13][C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)[CH:25]=[CH:24][C:23]=2[O:26][CH3:27])[CH2:30][CH2:31][CH2:32][CH2:33]1

Participants

6

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57252838HCID 57252838, compound

Product 1

HCID 54132651HCID 54132651, compoundYield 39.4%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]-phenylacetaldehyde diethyl acetal from Step 4 (1.14 g, 2.33 mmol), pyridinium p-toluenesulfonate (0.761 g, 3.03 mmol) in acetone (30 mL) and water (1.3 mL) was heated to reflux for 20 h. It was then allowed to cool to room temperature, diluted with EtOAc, successively washed with 5% aqueous NaHCO3 (2×) and brine, dried (MgSO4) and concentrated. The residue was purified by column chromatography on silica (EtOAc/hexane 3:2→7:3→4:1→1:0) to afford the title compound as a white foam (0.381 g, 39%).

Workup

  1. temperatureto reflux for 20 h
  2. washsuccessively washed with 5% aqueous NaHCO3 (2×) and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica (EtOAc/hexane 3:2→7:3→4:1→1:0)

Sources & evidence

ORD record
ord-5320b5111cca4740965602a8d553bede
Source dataset
uspto-grants-1998_01
Patent number
US05710170

Reaction notes

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