Hydrochloric Acid → 2-(1,6-Dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

HRID 1798131Notes

Reaction equation

HRID 1798131 reaction equation
[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]([CH2:13][C:14]([O:16]CC)=[O:15])[O:3]1.[Li+].[OH-].Cl>CO.O>[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]([CH2:13][C:14]([OH:16])=[O:15])[O:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292549Ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 582927912-(1,6-Dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(1,6-dihydroxy-4-methyl-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (300 mg, 1.2 mmol) in MeOH (2 mL) was added LiOH (144 mg, 6 mmol) in 5 ml H2O at 0° C. The reaction mixture was stirred at room temperature for 1.5 h and acidified by 1N HCl to pH=5.0. The resulting mixture was extracted with EtOAc (3×20 mL) and the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give a crude product, which was used directly in next step without further purification.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc (3×20 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7e5a42ba5fcb46108fe091f03b2ff31f
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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