Pyridine → (+)-(S)-3-(4-fluorophenoxy)-1,2-propanediol

HRID 1723434Notes

Reaction equation

HRID 1723434 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][C@H:8]([OH:11])[CH2:9][OH:10])=[CH:4][CH:3]=1.N1C=CC=CC=1.CC1C=CC(S(Cl)(=O)=O)=CC=1>ClC(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][C@@H:8]([OH:11])[CH2:9][OH:10])=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11321370(-)-(R)-3-(4-fluorophenoxy)-1,2-propanediol

Product 1

HCID 53648274(+)-(S)-3-(4-fluorophenoxy)-1,2-propanediolYield 67.2%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 11 parts of (-)-(R)-3-(4-fluorophenoxy)-1,2-propanediol, 23.3 parts of pyridine and 240 parts of trichloromethane were added 12.3 parts of 4-methylbenzenesulfonyl chloride. The whole was stirred overnight at room temperature. It was washed successively with acid water, a sodium carbonate solution and water, dried, filtered and evaporated. The residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (98:2 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 13.5 parts (67.2%) of (+)-(S)-3-(4-fluorophenoxy)-1,2-propanediol, O1 -4-methylbenzenesulfonate; [α]D =+11.11° (c=0.5% in trichloromethane) (147).

Workup

  1. washIt was washed successively with acid water
  2. dry with materiala sodium carbonate solution and water, dried
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue was purified by column chromatography over silica gel using
  6. additiona mixture of trichloromethane and methanol (98:2 by volume) as eluent
  7. customThe pure fractions were collected
  8. customthe eluent was evaporated

Sources & evidence

ORD record
ord-e74a9cbc8aaa4a0686375f4c58b91253
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

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