p-Toluenesulfonic acid monohydrate → HCID 22241594, compound

HRID 892197Notes

Reaction equation

HRID 892197 reaction equation
COCCOC[O:7][C:8]1[CH:9]=[C:10]([CH:20]=[CH:21][CH:22]=1)[CH2:11][O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.CCOC(C)=O>[N:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][O:12][CH2:11][C:10]1[CH:9]=[C:8]([OH:7])[CH:22]=[CH:21][CH:20]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 22241408HCID 22241408, compound

Product 1

HCID 22241594HCID 22241594, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 2-[3-(2-methoxy-ethoxymethoxy)-benzyloxymethyl]-pyridine (171 mg, 0.56 mmol, example 73) in CH3OH (1.9 mL) is added p-toluenesulfonic acid monohydrate (148 mg, 0.78 mmol). The mixture is heated to 60° C. and stirred for 1.5 hrs, then cooled to room temperature and diluted with EtOAc. The organic layer is washed with sat NaHCO3, brine, then dried over MgSO4 and concentrated to give the title compound as a white crystalline solid. MS (ESI) 216 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with sat NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-e8cf5134a14e410aa7007854d110cf9c
Source dataset
uspto-grants-2006_02
Patent number
US07005440B1

Reaction notes

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