4-Toluenesulfonyl chloride → HCID 17910741, compound

HRID 1790882Notes

Reaction equation

HRID 1790882 reaction equation
[CH3:1][C:2]1([C:7]2([CH2:10][CH2:11][OH:12])[CH2:9][CH2:8]2)[O:6][CH2:5][CH2:4][O:3]1.[C:13]1([CH3:23])[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][C:2]1([C:7]2([CH2:10][CH2:11][O:12][S:19]([C:16]3[CH:17]=[CH:18][C:13]([CH3:23])=[CH:14][CH:15]=3)(=[O:21])=[O:20])[CH2:9][CH2:8]2)[O:3][CH2:4][CH2:5][O:6]1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 22042297HCID 22042297, compound

Product 1

HCID 17910741HCID 17910741, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

470 mg of 9 is dissolved in 10 ml of pyridine, and p-toluenesulfonyl chloride is added at 0° C. under nitrogen. It is stirred for 1 hour at 0° C., and then sodium bicarbonate solution is added. It is extracted with ethyl acetate, washed with dilute hydrochloric acid and then with sodium bicarbonate solution, dried on sodium sulfate and concentrated by evaporation. After the residue is chromatographed on silica gel with ethyl acetate/hexane, 670 mg of the title compound remains as a colorless oil.

Workup

  1. extractionIt is extracted with ethyl acetate
  2. washwashed with dilute hydrochloric acid
  3. dry with materialwith sodium bicarbonate solution, dried on sodium sulfate
  4. concentrationconcentrated by evaporation
  5. customAfter the residue is chromatographed on silica gel with ethyl acetate/hexane, 670 mg of the title compound

Sources & evidence

ORD record
ord-00d9a39c35f54c10bf5709b7fb250eb9
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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