p-Toluenesulfonic acid → HCID 54001313, compound

HRID 865466Notes

Reaction equation

HRID 865466 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:34])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][C:30]([CH3:33])([OH:32])[CH3:31])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1.[O:35]1[CH:40]=[CH:39][CH2:38][CH2:37][CH2:36]1.CC1C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH:12]=[CH:13][C:14]3[CH:15]=[C:16]([C:20](=[O:34])[CH2:21][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[CH2:29][C:30]([O:32][CH:36]4[CH2:37][CH2:38][CH2:39][CH2:40][O:35]4)([CH3:31])[CH3:33])[CH:17]=[CH:18][CH:19]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 54436152HCID 54436152, compound

Product 1

HCID 54001313HCID 54001313, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the alcohol of Step 2 (390 g, 8.29 mmol), 3,4-dihydro-2H-pyran (7.4 mL, 81 mmol) and pyridinum p-toluenesulfonate (684 mg, 2.7 mmol) in 44 mL of CH2Cl2 was heated at reflux for 23 hours. The reaction mixture was allowed to cool to r.t. and 10% aq. NaHCO3 was added. The title product was extracted with CH2Cl2, dried over Na2SO4 and purified by flash chromatography on silica using EtOAc:toluene 5:95. Yield: 4.22 g, 92%.

Workup

  1. temperatureat reflux for 23 hours
  2. extractionThe title product was extracted with CH2Cl2
  3. dry with materialdried over Na2SO4
  4. custompurified by flash chromatography on silica

Sources & evidence

ORD record
ord-a0bfcaf2bba04e47b0e922c6fccf6012
Source dataset
uspto-grants-1996_10
Patent number
US05565473

Reaction notes

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