Methanesulfonyl chloride → HCID 54086722, compound

HRID 846733Notes

Reaction equation

HRID 846733 reaction equation
[F:1][C:2]1[CH:13]=[CH:12][C:5]([O:6][CH2:7][CH2:8][CH:9]([OH:11])[CH3:10])=[CH:4][CH:3]=1.[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:14][S:15]([O:11][CH:9]([CH2:8][CH2:7][O:6][C:5]1[CH:12]=[CH:13][C:2]([F:1])=[CH:3][CH:4]=1)[CH3:10])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 15096976HCID 15096976, compound

Product 1

HCID 54086722HCID 54086722, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred and cooled mixture of 10 parts of 4-(4-fluorophenoxy)-2-butanol and 30 parts of pyridine were added portionwise 7.4 parts of methanesulfonyl chloride at a temperature below 10° C. Upon completion, stirring was continued for 1 hour at room temperature. The reaction mixture was allowed to stand overnight in an ice-box. Then it was poured onto water and the product was extracted with dichloromethane. The extract was washed with a cold hydrochloric acid solution 20% and with water, dried, filtered and evaporated. The oily residue was purified by column-chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 10 parts (64%) of 4-(4-fluorophenoxy)-2-butanol methanesulfonate (ester) as an oily residue (intermediate 28).

Workup

  1. temperaturecooled
  2. stirringUpon completion, stirring
  3. waitto stand overnight in an ice-box
  4. additionThen it was poured onto water
  5. extractionthe product was extracted with dichloromethane
  6. washThe extract was washed with a cold hydrochloric acid solution 20% and with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe oily residue was purified by column-chromatography over silica gel using
  11. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  12. customThe pure fractions were collected
  13. customthe eluent was evaporated

Sources & evidence

ORD record
ord-9210da69fcaa427787531131c13f637f
Source dataset
uspto-grants-1992_08
Patent number
US05137896

Reaction notes

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