Pyridine → 3,6,9,12,15-Pentaoxaheptadecane-1,17-diol, 1-4-methylbenzenesulfonate

HRID 990215Notes

Reaction equation

HRID 990215 reaction equation
[CH2:1]([OH:19])[CH2:2][O:3][CH2:4][CH2:5][O:6][CH2:7][CH2:8][O:9][CH2:10][CH2:11][O:12][CH2:13][CH2:14][O:15][CH2:16][CH2:17][OH:18].N1C=CC=CC=1.[S:26](Cl)([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]>C(Cl)Cl>[S:26]([O:18][CH2:17][CH2:16][O:15][CH2:14][CH2:13][O:12][CH2:11][CH2:10][O:9][CH2:8][CH2:7][O:6][CH2:5][CH2:4][O:3][CH2:2][CH2:1][OH:19])([C:29]1[CH:35]=[CH:34][C:32]([CH3:33])=[CH:31][CH:30]=1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 17472Hexaethylene Glycol

Product 1

HCID 104331623,6,9,12,15-Pentaoxaheptadecane-1,17-diol, 1-4-methylbenzenesulfonateYield 80.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

25 g (88.5 mmol) of hexaethyleneglycol was stirred at 0° C. in 200 mL of CH2Cl2, and 14.3 mL of pyridine (177 mmol; 2 eq.) was added to the mixture followed by 17.4 g (88.5 mmol) of tosylchloride. The reaction mixture was stirred at room temperature for 24 hours and partitioned between 400 ml of 1N HCl and 200 ml of CH2Cl2. The organic layer was dried over MgSO4, filtered, and concentrated to provide 31 g of a light yellow oil. Purification by silica gel chromatography (CH2Cl2/MeOH) provided 15.32 g (40%) of 1 as a light yellow oil: 1H NMR (CDCl3) δ2.45 (s, 3H), 3.55-3.75 (m, 22H), 4.15 (t, 2H), 7.35 (d, 2H), 7.80 (d, 2H); HRMS (FAB) calculated for C19H33O9S (M+H): 437.1845. Found: 437.1834.

Workup

  1. custompartitioned between 400 ml of 1N HCl and 200 ml of CH2Cl2
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-843c4ab8855e4c92aa3efec1ff286885
Source dataset
uspto-grants-2002_10
Patent number
US06458953B1

Reaction notes

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