Hydrochloric Acid → (S)-1-(3-Methylphenyl)-1,2-ethanediol 2-tosylate

HRID 618283Notes

Reaction equation

HRID 618283 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C@H:8]([OH:11])[CH2:9][OH:10])[CH:5]=[CH:6][CH:7]=1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.Cl>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[S:18]([O:10][CH2:9][C@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=1)[OH:11])([C:15]1[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=1)(=[O:20])=[O:19]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 54443561HCID 54443561, compound

Product 1

HCID 53847205(S)-1-(3-Methylphenyl)-1,2-ethanediol 2-tosylateYield 84.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

To a stirred solutioll of (S)-1-(3-methylphenyl)-1,2-ethanediol (1.78 g, 11.7 mmol) in pyridine (35 ml) was added p-toluenesulfonyl chloride (2.46 g, 12.9 mmol), and 4-dimethylaminopyridine (1.58 g, 12.9mmol) at 0° C. and the reaction mixture was stirred at 0° C. to rt for 17 h. The reaction mixture was acidified with 6 N HCl aqueous solution and extracted with CH2Cl2. The extract was washed with water and brine, dried (Na2SO4), and concentrated to give 3.02 g of yellow oil, which was purified by column chromatography (silica gel: 100 g, ethyl acetatelhexane:1/9 to 1/3) to afford 2.63 g (73%) of desired product as light yellow oil. Its optical purity was 97% ee by HPLC employing a chiral stationary phase (chiral pak AS, Daicel Chemical Industries, eluted with n-hexane/EtOH:98/2; detection time:: 55 min for (R)-isomer 59 min for (S)-isomer).

Workup

  1. extractionextracted with CH2Cl2
  2. washThe extract was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c4ced49408a4ee4a2c09e916a6080c1
Source dataset
uspto-grants-1999_09
Patent number
US05952369

Reaction notes

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