Pyridine → (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane

HRID 973342Notes

Reaction equation

HRID 973342 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][C@@H:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:9][CH2:10][CH2:11][OH:12].N1C=CC=CC=1.[CH3:24][S:25](Cl)(=[O:27])=[O:26]>CCOCC>[CH3:24][S:25]([O:12][CH2:11][CH2:10][CH2:9][C@@H:8]([O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])(=[O:27])=[O:26]

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 68122110(4S)-4-(2-tetrahydropyranyloxy)-1-nonanol

Product 1

HCID 86735174(4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of (4S)-4-(2-tetrahydropyranyloxy)-1-nonanol (29.2 g., 0.12 mole) and pyridine (20 ml.) is cooled to 5° by means of an ice bath. Methanesulfonyl chloride (17.2 g., 0.15 mole) is added dropwise during 20 minutes and the mixture is stirred 4 hours with ice bath cooling. The mixture is then taken up in ether, washed with 4 portions of water and with brine and dried over sodium sulfate. The ether is distilled on the rotary evaporator to leave as a residual oil crude (4S)-1-methylsulfonyloxy-4-(2-tetrahydropyranyloxy)-nonane.

Workup

  1. temperatureis cooled to 5° by means of an ice bath
  2. temperaturecooling
  3. washwashed with 4 portions of water and with brine
  4. dry with materialdried over sodium sulfate
  5. distillationThe ether is distilled on the rotary evaporator

Sources & evidence

ORD record
ord-a2993c0c420e4b8caa5a979a34756f79
Source dataset
uspto-grants-1977_10
Patent number
US04055597

Reaction notes

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