Hydrochloric Acid → HCID 58292790, compound

HRID 1798108Notes

Reaction equation

HRID 1798108 reaction equation
[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[CH:4]([CH2:15][C:16]([O:18]CC)=[O:17])[O:3]1.[OH-].[Li+].Cl>CO>[OH:1][B:2]1[C:6]2[CH:7]=[C:8]([O:13][CH3:14])[CH:9]=[C:10]([O:11][CH3:12])[C:5]=2[CH:4]([CH2:15][C:16]([OH:18])=[O:17])[O:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 58292634HCID 58292634, compound

Product 1

HCID 58292790HCID 58292790, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl 2-(1-hydroxy-4,6-dimethoxy-1,3-dihydrobenzo[c][1,2]oxaborol-3-yl)acetate (0.28 g, 1.0 mmol) in methanol (5 mL) was added dropwise an aqueous solution of lithium hydroxide (2N, 2.5 mL) at 0° C. The reaction mixture was stirred at room temperature for 3 hr and acidified to pH=2 with diluted hydrochloride acid. The resulting mixture was extracted with ethyl acetate (2×20 mL), the combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give the title compound as a white solid (0.23 g, Yield: 92%). 1H NMR (400 Hz, CDCl3) δ 12.27 (s, 1H), 9.18 (s, 1H), 6.80-6.81 (d, J=2.0 Hz, 1H), 6.63-6.64 (d, J=4.0 Hz, 1H), 5.35-5.38 (m, 1H), 3.81 (s, 3H), 3.78 (s, 3H), 3.07-3.11 (m, 1H), 2.04-2.10 (m, 1H); MS (ESI) m/z=253 [M+H]+.

Workup

  1. extractionThe resulting mixture was extracted with ethyl acetate (2×20 mL)
  2. dry with materialthe combined organic layers were dried over anhydrous Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-ab99abcd2a4645bc9d34aec0e4fe932b
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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