4-Toluenesulfonyl chloride → (4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl 4-methylbenzenesulfonate

HRID 31729Notes

Reaction equation

HRID 31729 reaction equation
[CH3:1][C:2]1([CH3:20])[O:7][CH2:6][CH:5]([CH2:8][O:9][C:10]2[C:15]([CH3:16])=[CH:14][N:13]=[C:12]([CH2:17][OH:18])[C:11]=2[CH3:19])[CH2:4][O:3]1.[OH-].[Na+].[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>O1CCCC1>[CH3:33][C:23]1[CH:28]=[CH:27][C:26]([S:29]([O:18][CH2:17][C:12]2[C:11]([CH3:19])=[C:10]([O:9][CH2:8][CH:5]3[CH2:6][O:7][C:2]([CH3:20])([CH3:1])[O:3][CH2:4]3)[C:15]([CH3:16])=[CH:14][N:13]=2)(=[O:31])=[O:30])=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 57445208(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methanol

Product 1

HCID 59792411(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl 4-methylbenzenesulfonateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a tetrahydrofuran (30 ml) solution of (4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methanol (738 mg, 2.61 mmol), powdered sodium hydroxide (313 mg, 7.84 mmol) was added and the mixture was stirred at room temperature for 35 minutes. The mixture was further stirred for 10 minutes under ice-cool and p-toluenesulfonyl chloride (1.09 g, 5.74 mmol) was added little by little for one minute. The reaction mixture was stirred at room temperature for 17 hours and 40 minutes and diluted with tetrahydrofuran, and then insoluble substance was removed by filtration. To the filtrate, silica gel was added, and the mixture was concentrated, and subjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1) to obtain the title compound (1.00 g, 88%) as a white solid.

Workup

  1. stirringThe mixture was further stirred for 10 minutes under ice-
  2. temperaturecool
  3. stirringThe reaction mixture was stirred at room temperature for 17 hours and 40 minutes
  4. custominsoluble substance was removed by filtration
  5. additionTo the filtrate, silica gel was added
  6. concentrationthe mixture was concentrated
  7. washsubjected to silica gel column chromatography (elution solvent: n-heptane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-a23b6307692247818521bde3fbb626d3
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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