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

HRID 2366042Notes

Reaction equation

HRID 2366042 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-82bd770c2024462f8e061083001b85aa
Source dataset
uspto-grants-2014_04
Patent number
US08697723B2

Reaction notes

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