Water → (4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl methanesulfonate

HRID 31727Notes

Reaction equation

HRID 31727 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.O.C(N(CC)CC)C.[CH3:29][S:30](Cl)(=[O:32])=[O:31]>C1(C)C=CC=CC=1.O1CCCC1.C(OCC)(=O)C>[CH3:29][S:30]([O:18][CH2:17][C:12]1[C:11]([CH3:19])=[C:10]([O:9][CH2:8][CH:5]2[CH2:6][O:7][C:2]([CH3:20])([CH3:1])[O:3][CH2:4]2)[C:15]([CH3:16])=[CH:14][N:13]=1)(=[O:32])=[O:31]

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 57445208(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methanol

Product 1

HCID 59792581(4-((2,2-Dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methyl methanesulfonateYield 93.3%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(4-((2,2-dimethyl-1,3-dioxan-5-yl)methoxy)-3,5-dimethylpyridin-2-yl)methanol (2.5 g, 8.35 mmol as the water content was regarded as 7.28%) was dissolved in toluene and the mixture was subjected twice to azeotropic dehydration. The residue was dissolved in tetrahydrofuran (30 ml). To the solution, triethylamine (2.33 ml, 16.7=mol) was added and the mixture was stirred in nitrogen atmosphere under ice-cool. Further, methanesulfonyl chloride (0.766 ml, 10 mmol) was added dropwise at an inner temperature below 11.5° C. for 2 minutes. The reaction mixture was stirred for 13 minutes under the same conditions, diluted with ethyl acetate and washed with a saturated aqueous sodium hydrogencarbonate solution and a saturated saline solution. The organic layer was dried over magnesium sulfate and filtrated through silica gel and the filtrate was concentrated under reduced pressure to obtain the title compound (2.8 g, 93.3%) as a light orange solid.

Workup

  1. temperaturecool
  2. stirringThe reaction mixture was stirred for 13 minutes under the same conditions
  3. washwashed with a saturated aqueous sodium hydrogencarbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltrated through silica gel
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-50d01f3b1acb41519eba9404c5fe5fa6
Source dataset
uspto-grants-2008_09
Patent number
US07425634B2

Reaction notes

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