Tetrahydropyran-2-methanol → 99335-60-1

HRID 1385866Notes

Reaction equation

HRID 1385866 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[CH3:9][S:10](Cl)(=[O:12])=[O:11].C(N(CC)CC)C.C(OC)(C)(C)C>C1(C)C=CC=CC=1.O>[CH3:9][S:10]([O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)(=[O:12])=[O:11]

Participants

7

Reactant 4

HCID 7524Tetrahydropyran-2-methanolHCID 8471TriethylamineHCID 15413tert-Butyl methyl etherHCID 31297Methanesulfonyl chloride

Product 1

HCID 28811599335-60-1

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

In 200 ml of toluene, 23.2 g (200 mmol) of tetrahydropyran-2-ylmethanol were admixed with 27.5 g (240 mmol) of methanesulfonyl chloride. At 10° C., 24.3 g (240 mmol) of triethylamine were then added dropwise, and stirring was continued for 2 hours at room temperature. 200 ml of methyl tert-butyl ether and 200 ml of water were then added to the mixture and the organic phase was separated off, washed with 200 ml of water and dried. Removal of the solvent under reduced presure gave 33.7 g (87% of theory) of a clear oil. (1H-NMR (CDCl3; δ in ppm): 4.20 (d,2H); 4.05 (dd,1H); 3.60 (m,1H); 3.45 (m,1H); 3.1 (s,3H); 1.95 (m,1H); 1.45 (m,5H))

Workup

  1. customthe organic phase was separated off
  2. washwashed with 200 ml of water
  3. customdried
  4. customRemoval of the solvent under reduced presure
  5. customgave 33.7 g (87% of theory) of a clear oil

Sources & evidence

ORD record
ord-fd407ce9bea248d6a11d1bb128e808ee
Source dataset
uspto-grants-2001_07
Patent number
US06265352B1

Reaction notes

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