Pyridine → HCID 59398279, compound

HRID 39749Notes

Reaction equation

HRID 39749 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1([OH:14])[CH2:13][CH2:12][C:7]2([O:11][CH2:10][CH2:9][O:8]2)[CH2:6][CH2:5]1.N1C=CC=CC=1.[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.O>[CH3:31][C:21]1[CH:26]=[CH:25][C:24]([S:27]([O:1][CH2:2][CH2:3][C:4]2([OH:14])[CH2:13][CH2:12][C:7]3([O:11][CH2:10][CH2:9][O:8]3)[CH2:6][CH2:5]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 112179178-(2-Hydroxyethyl)-1,4-dioxaspiro[4.5]decan-8-ol

Product 1

HCID 59398279HCID 59398279, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To 30 mL of a chloroform solution containing 4.2 g of 8-(2-hydroxyethyl)-1,4-dioxaspiro(4.5)decan-8-ol, 2.18 mL of pyridine was added at room temperature, and 4.0 g of p-toluenesulfonyl chloride was dividedly added thereto under cooling with ice, the mixture was stirred at room temperature for 1 hour and 35 minutes, left to stand overnight, and then further stirred at 30 to 40° C. for 1 hour. The reaction mixture was added with water and chloroform under cooling with ice. The organic layer was separated, washed with an aqueous saturated sodium chloride solution, and then dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=50:1] to obtain 4.2 g of a yellow oily substance, 2-(8-hydroxy-1,4-dioxaspiro(4.5)decan-8-yl)ethyl 4-methylbenzenesulfonate.

Workup

  1. additionwas added at room temperature
  2. temperatureunder cooling with ice
  3. waitleft
  4. waitto stand overnight
  5. stirringfurther stirred at 30 to 40° C. for 1 hour
  6. temperatureunder cooling with ice
  7. customThe organic layer was separated
  8. washwashed with an aqueous saturated sodium chloride solution
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customthe solvent was removed under reduced pressure
  11. customThe residue thus obtained
  12. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=50:1]

Sources & evidence

ORD record
ord-60f66cf61fef40559daeef0bdd45ae3e
Source dataset
uspto-grants-2013_09
Patent number
US08524738B2

Reaction notes

Loading…