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

HRID 1872758Notes

Reaction equation

HRID 1872758 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 solution 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, 12.9 mmol) at 0° C. and the reaction mixture was stirred at 0° C. to rt for 17 h. The reaction mixture was acidified with 6N 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 acetate/hexane: 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-4c7f96a5fd334cc6bc8b9d04ff1d162b
Source dataset
uspto-grants-2000_08
Patent number
US06110947

Reaction notes

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