4-Toluenesulfonyl chloride → HCID 14986677, compound

HRID 1494119Notes

Reaction equation

HRID 1494119 reaction equation
[OH:1][CH:2]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1.C(N(CC)CC)C.[C:30]1([CH3:40])[CH:35]=[CH:34][C:33]([S:36](Cl)(=[O:38])=[O:37])=[CH:32][CH:31]=1>C(Cl)Cl.CN(C)C1C=CN=CC=1.CCOCC>[S:36]([O:1][CH:2]([CH2:14][CH2:15][CH2:16][C:17]1[CH:18]=[N:19][CH:20]=[CH:21][CH:22]=1)[CH2:3][CH2:4][CH2:5][CH2:6][O:7][CH:8]1[CH2:13][CH2:12][CH2:11][CH2:10][O:9]1)([C:33]1[CH:34]=[CH:35][C:30]([CH3:40])=[CH:31][CH:32]=1)(=[O:38])=[O:37]

Participants

7

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 10335383HCID 10335383, compound

Product 1

HCID 14986677HCID 14986677, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.405 g (1.3 mmol) 5-hydroxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane in 8 mL methylene chloride is added a few crystals of 4-dimethylaminopyridine followed by 0.5 mL (3.6 mmol) triethylamine and 0.5 g (2.6 mmol) p-toluenesulfonyl chloride. The reaction is stirred at room temperature for 18 hours and then diluted with ether. The ether layer is washed with saturated aqueous sodium bicarbonate, dried, filtered and evaporated to give an amber oil which is purified by chromatography over silica gel using ether/ethyl acetate (4:1) as eluent to yield 5-tosyloxy-8-(3-pyridyl)-1-(2-tetrahydropyranyloxy)-octane; NMR (CDCl3): delta 7.9 (d,2H), 7.4 (d,2H), 2.45 (s,3H).

Workup

  1. washThe ether layer is washed with saturated aqueous sodium bicarbonate
  2. customdried
  3. filtrationfiltered
  4. customevaporated
  5. customto give an amber oil which
  6. customis purified by chromatography over silica gel

Sources & evidence

ORD record
ord-d725356aabaa4466b4c264ba66ae8867
Source dataset
uspto-grants-1991_06
Patent number
US05025025

Reaction notes

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