p-Toluenesulfonate → HCID 68527750, compound

HRID 2221307Notes

Reaction equation

HRID 2221307 reaction equation
[C:1]1([S:7]([C:10]2[CH:24]=[CH:23][C:13]([O:14][CH2:15][C@@H:16]3[CH2:20]CC(C)(C)[O:17]3)=[C:12]([Br:25])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C)C=CC(S([O-])(=O)=[O:33])=CC=1>CC(C)=O.O>[C:1]1([S:7]([C:10]2[CH:24]=[CH:23][C:13]([O:14][CH2:15][C@H:16]([OH:17])[CH2:20][OH:33])=[C:12]([Br:25])[CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 85570p-ToluenesulfonateHCID 68525779HCID 68525779, compound

Product 1

HCID 68527750HCID 68527750, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of 4-(S)-(4-benzenesulfonyl-2-bromo-phenoxymethyl)-2,2-dimethyl-[3,3]dioxolan (1.07 g, 0.0025 mol) and pyridinum toluene-4-sulfonate (0.38 g, 0.0015 mol) in acetone (20 mL) and water (5 mL) was heated under reflux for 12 hours. The solvent was removed under reduced pressure. The oily residue was dissolved in ethyl acetate (100 mL), washed with cold 10% aqueous hydrochloric acid, saturated sodium bicarbonate, dried (Na2SO4) and concentrated in vacuo. Recrystallization of the residue (diethyl ether-hexane) gave 3-(4-benzenesulfonyl-2-bromo-phenoxy)-propane 1-2-(R)-diol as white crystals. Mp. 104.6-105.9° C.

Workup

  1. temperatureunder reflux for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. dissolutionThe oily residue was dissolved in ethyl acetate (100 mL)
  4. washwashed with cold 10% aqueous hydrochloric acid, saturated sodium bicarbonate
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customRecrystallization of the residue (diethyl ether-hexane)

Sources & evidence

ORD record
ord-a207f1aad45843e7b2027ed71c85f764
Source dataset
uspto-grants-2008_05
Patent number
US07368567B2

Reaction notes

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