Potassium Carbonate → Methanesulfonic acid (R)-5-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl ester

HRID 453834Notes

Reaction equation

HRID 453834 reaction equation
[OH:1][C:2]1[CH:21]=[CH:20][CH:19]=[C:18]([OH:22])[C:3]=1[O:4][CH2:5][C@H:6](OS(C)(=O)=O)[CH2:7][O:8][S:9]([CH3:12])(=[O:11])=[O:10].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[OH:1][C:2]1[C:3]2[O:4][CH2:5][C@H:6]([CH2:7][O:8][S:9]([CH3:12])(=[O:10])=[O:11])[O:22][C:18]=2[CH:19]=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86644726Methanesulfonic acid (S)-3-(2,6-dihydroxy-phenoxy)-2-methanesulfonyloxy-propyl ester

Product 1

HCID 86644727Methanesulfonic acid (R)-5-hydroxy-2,3-dihydro-benzo[1,4]dioxin-2-ylmethyl esterYield 40.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulfonic acid (S)-3-(2,6-dihydroxy-phenoxy)-2-methanesulfonyloxy-propyl ester (253 g, 7.10 mmol) and potassium carbonate (1.14 g, 8.30 mmol) in acetone (30 ml) was refluxed under nitrogen atmosphere for 3.5 h. The reaction mixture was cooled down, filtered and evaporated to dryness. The crude product was purified with flash chromatography using dichloromethane and ethyl acetate as eluents to give 0.75 g of the title compound.

Workup

  1. temperaturewas refluxed under nitrogen atmosphere for 3.5 h
  2. temperatureThe reaction mixture was cooled down
  3. filtrationfiltered
  4. customevaporated to dryness
  5. customThe crude product was purified with flash chromatography

Sources & evidence

ORD record
ord-dc3b51afedcd4e369ad41f3e9235466a
Source dataset
uspto-grants-2013_07
Patent number
US08492549B2

Reaction notes

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