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

HRID 1798117Notes

Reaction equation

HRID 1798117 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][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[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][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[O:3]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 67252473tert-butyl 2-(1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292793tert-Butyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetateYield 71.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of tert-butyl 2-(1-hydroxy-4-methyl-6-(tetrahydro-2H-pyran-2-yloxy)-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (2.2 g, 6.07 mmol) in 15 mL THF was added 2N HCl (6 mL) at 0° C. The mixture was stirred overnight at room temperature and concentrated in vacuo. The residue was purified by column to give the desired product (1.2 g, yield: 71%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by column

Sources & evidence

ORD record
ord-9a4186096d8a4ab0b9b99d0dc36e4158
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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