4-Toluenesulfonyl chloride → 4-Methoxy-2-p-toluenesulfonyloxymethylpyridine

HRID 1741007Notes

Reaction equation

HRID 1741007 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][N:4]=1.[C:11]1([CH3:21])[CH:16]=[CH:15][C:14]([S:17](Cl)(=[O:19])=[O:18])=[CH:13][CH:12]=1.C(N(CC)CC)C>C(Cl)Cl>[CH3:10][O:9][C:7]1[CH:6]=[CH:5][N:4]=[C:3]([CH2:2][O:1][S:17]([C:14]2[CH:15]=[CH:16][C:11]([CH3:21])=[CH:12][CH:13]=2)(=[O:19])=[O:18])[CH:8]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10820596(4-Methoxy-pyridin-2-yl)-methanol

Product 1

HCID 218343624-Methoxy-2-p-toluenesulfonyloxymethylpyridineYield 103.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

The 2-hydroxymethyl-4-methoxypyridine, (3.48 g, 0.024 mol) was dissolved in 50 ml CH2Cl2 and cooled to 0° C. The p-toluenesulfonyl chloride (5.7 g, 0.03 mol) was added followed by triethylamine (5 g), in 10 ml of CH2Cl2. After 15 minutes, the reaction was stirred at room temperature for one hour. The reaction was diluted with CH2Cl2 (200 ml) and washed with water. The organic layer was separated and dried with MgSO4, filtered and concentrated to afford 7.3 g of crude subtitle compound suitable for further use.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-529afc0034b9436f8c06c3d3605ef849
Source dataset
uspto-grants-1999_10
Patent number
US05972972

Reaction notes

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