Methanesulfonyl chloride → HCID 88246547, compound

HRID 2289375Notes

Reaction equation

HRID 2289375 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@H:8]([CH2:11][C@@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16])[CH2:9][OH:10].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH3:18][S:19]([O:10][CH2:9][C@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:11][C@@H:12]([CH3:17])[CH2:13][CH2:14][CH2:15][CH3:16])(=[O:21])=[O:20]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 70269844HCID 70269844, compound

Product 1

HCID 88246547HCID 88246547, compoundYield 87.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 1.51 g of (2R,4S)-2-tetrahydropyranyloxy-4-methyloctanol obtained in Step 9 and 15 ml of pyridine was kept at -5° C., and 1.06 g of methanesulfonyl chloride was added thereto, followed by stirring at that temperature for 1 hour. The reaction mixture was poured into ice-water and extracted with diethyl ether. The extract was adjusted to pH 5 with 1% hydrochloric acid, washed with water, dried, and distilled to remove the solvent to obtain 1.74 g (77.81%) of the titled compound.

Workup

  1. customwas kept at -5° C.
  2. extractionextracted with diethyl ether
  3. washwashed with water
  4. customdried
  5. distillationdistilled
  6. customto remove the solvent

Sources & evidence

ORD record
ord-1d84292b99d7470d832e0242315a5b39
Source dataset
uspto-grants-2000_07
Patent number
US06093345

Reaction notes

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