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

HRID 2407329Notes

Reaction equation

HRID 2407329 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-ebad085d7cbd480d8d6f42feb976a659
Source dataset
uspto-grants-2014_08
Patent number
US08809536B2

Reaction notes

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