Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → 4-Methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran

HRID 21900Notes

Reaction equation

HRID 21900 reaction equation
[CH3:1][O:2][C:3]1([C:9]#[C:10][CH2:11][O:12]C2CCCCO2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>CO>[CH3:1][O:2][C:3]1([C:9]#[C:10][CH2:11][OH:12])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 199309164-Methoxy-4-[3-(tetrahydropyran-2-yloxy)prop-1-ynyl]tetrahydropyran

Product 1

HCID 193880394-Methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyranYield 47.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-methoxy-4-[3-(tetrahydropyran-2-yloxy)-prop-1-ynyl]tetrahydropyran (3.8 g, 14.8 mmol), prepared as in step 2, in methanol (50 mL), was added a catalytic amount of pyridinium p-toluenesulfonate (PPTS). The resulting yellow solution was stirred under nitrogen for 17 hours at ambient temperature. The volatiles were removed in vacuo and the residue was dissolved in ethyl acetate and treated with saturated aqueous NH4Cl. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 30% ethyl acetate: hexanes) provided 4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran (1.2 g, 47 %) as a colorless oil.

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. additiontreated with saturated aqueous NH4Cl
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (100 g, 30% ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-22633109d3af45cc92382ba23aff32c0
Source dataset
uspto-grants-1995_06
Patent number
US05426111

Reaction notes

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