Hydrochloric Acid → Methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

HRID 1798321Notes

Reaction equation

HRID 1798321 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:12]C3CCCCO3)[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:19][S:20]([O:23][CH3:24])(=[O:22])=[O:21])[O:3]1.Cl>C1COCC1>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([OH:12])[CH:9]=[C:10]([CH3:11])[C:5]=2[CH:4]([CH2:19][S:20]([O:23][CH3:24])(=[O:22])=[O:21])[O:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58292744Methyl (1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

Product 1

HCID 58292585Methyl (1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of methyl (1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)methanesulfonate (1.64 g) in THF cooled at −20° C. was added 6N HCl until pH=1. After the mixture was stirred at −20° C. for 20 minutes, concentrate. The residue was purified by flash chromatography to give desired product as an off-white solid.

Workup

  1. concentrationconcentrate
  2. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-6e8f5864c3bd4b20818e26302493f2e4
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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