Methanesulfonyl chloride → Oxan-4-yl methanesulfonate

HRID 386866Notes

Reaction equation

HRID 386866 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[CH3:8][S:9](Cl)(=[O:11])=[O:10]>C1(C)C=CC=CC=1.C(N(CC)CC)C>[O:1]1[CH2:6][CH2:5][CH:4]([O:7][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 74956Tetrahydro-4H-pyran-4-ol

Product 1

HCID 11344352Oxan-4-yl methanesulfonateYield 94.1%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
2 °C

Procedure

10 kg tetrahydropyran-4-ol are dissolved in a mixture of 50 L toluene and 10.4 kg triethylamine. 11.55 kg methanesulfonyl chloride in 100 ml toluene are added while maintaining the internal temperature below 20° C. by cooling, and the addition funnel is rinsed with 50 ml toluene. The stirring is continued for one hour. The precipitate is filtered and the filter cake is washed twice with 20 L toluene each. The filtrate is concentrated by vaccum evaporation (60 L were distilled of), seeding crystals and 50 L methylcyclohexane are added. The suspension is cooled to 2° C. After 1 h the product is isolated by filtration, washed with 30 L methylcyclohexane and dried at 30° C. 16.6 kg of the product are obtained as a white solid. Yield: 94%; 1H NMR (400 MHz, DMSO-d6) δ ppm 1.62-1.73 (2H, m), 1.92-2.00 (2 H, m), 3.19 (3H, s), 3.42-3.49 (2H, m), 3.77-3.83 (2H, m), 4.80-4.88 (1H, m).

Workup

  1. temperaturewhile maintaining the internal temperature below 20° C.
  2. temperatureby cooling
  3. washthe addition funnel is rinsed with 50 ml toluene
  4. filtrationThe precipitate is filtered
  5. washthe filter cake is washed twice with 20 L toluene each
  6. concentrationThe filtrate is concentrated by vaccum evaporation (60 L were distilled of)
  7. additionare added
  8. customAfter 1 h the product is isolated by filtration
  9. washwashed with 30 L methylcyclohexane
  10. customdried at 30° C

Sources & evidence

ORD record
ord-ba0f0a17ed464dba8c03f9b50bb6c5b3
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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