p-Toluenesulfonic acid monohydrate → HCID 59594666, compound

HRID 2263421Notes

Reaction equation

HRID 2263421 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][C:11]([CH2:22][O:23][C:24]3[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([CH3:32])[CH:25]=3)=[C:12]([CH2:14][O:15]C3CCCCO3)[N:13]=2)=[CH:5][CH:4]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[OH:15][CH2:14][C:12]1[N:13]=[C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)[O:10][C:11]=1[CH2:22][O:23][C:24]1[CH:31]=[CH:30][C:27]([C:28]#[N:29])=[C:26]([CH3:32])[CH:25]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 59594719HCID 59594719, compound

Product 1

HCID 59594666HCID 59594666, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.96 g 4-[2-(4-Methoxy-phenyl)-4-(tetrahydro-pyran-2-yloxymethyl)-oxazol-5-ylmethoxy]-2-methyl-benzonitrile were dissolved in 100 ml methanol. 522 mg p-toluenesulfonic acid monohydrate were added and the reaction mixture stirred at room temperature for one hour. The solvent was removed in vacuo. The residue was dissolved in 150 ml ethyl acetate and washed with 80 ml saturated NaHCO3 solution and brine. The organic phase was dried over MgSO4 and the solvent was evaporated in vacuo to obtain 4.1 g 4-[4-hydroxymethyl-2-(4-methoxy-phenyl)-oxazol-5-ylmethoxy]-2-methyl-benzonitrile as pale yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionThe residue was dissolved in 150 ml ethyl acetate
  3. washwashed with 80 ml saturated NaHCO3 solution and brine
  4. dry with materialThe organic phase was dried over MgSO4
  5. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-17fed3587d7d4b24b4807bf3739234c9
Source dataset
uspto-grants-2010_12
Patent number
US07851493B2

Reaction notes

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