Water → HCID 19004293, compound

HRID 2225838Notes

Reaction equation

HRID 2225838 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[CH2:8][CH2:9][CH2:10][OH:11].O>N1C=CC=CC=1>[S:2]([O:11][CH2:10][CH2:9][CH2:8][CH:7]([C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH:13]=1)[OH:6])([CH3:1])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 19004311HCID 19004311, compound

Product 1

HCID 19004293HCID 19004293, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methanesulfonyl chloride (0.77 g was added slowly with stirring to a cooled (-40° C.) solution of rac-delta-hydroxy-2-naphthalenebutanol (1.45 g) in dry pyridine (6 mL). The mixture was stirred at -40° C. for 5 hours, then was poured into water (20 mL) and extracted with ethyl acetate (3×10 mL). The combined organic layers were washed in turn with water (2×10 mL), saturated magnesium sulfate solution (3×15 mL) and brine, then were dried (MgSO4) and evaporated. The resulting oil was purified by HPLC (ethyl acetate-hexane; 2:3) to provide 1.25 g of rac-alpha-(3-mesyloxypropyl)-2-naphthalenemethanol as an oil.

Workup

  1. stirringThe mixture was stirred at -40° C. for 5 hours
  2. extractionextracted with ethyl acetate (3×10 mL)
  3. washThe combined organic layers were washed in turn with water (2×10 mL), saturated magnesium sulfate solution (3×15 mL) and brine
  4. dry with materialwere dried (MgSO4)
  5. customevaporated
  6. customThe resulting oil was purified by HPLC (ethyl acetate-hexane; 2:3)

Sources & evidence

ORD record
ord-0beb681e4efa44d2b8d38b1d9cff8059
Source dataset
uspto-grants-1994_09
Patent number
US05344843

Reaction notes

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