Hydrochloric Acid → HCID 86664738, compound

HRID 2367985Notes

Reaction equation

HRID 2367985 reaction equation
[O:1]1CCO[CH:2]1[C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([O:12][CH2:13][CH3:14])[C:7]=1[B:15]([O:20]C(C)C)[O:16]C(C)C.Cl.[OH-].[Na+]>C1COCC1>[CH2:13]([O:12][C:8]1[CH:9]=[CH:10][CH:11]=[C:6]([CH:2]=[O:1])[C:7]=1[B:15]([OH:20])[OH:16])[CH3:14]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66691352HCID 66691352, compound

Product 1

HCID 86664738HCID 86664738, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the mixture of diisopropyl 2-(1,3-dioxolan-2-yl)-6-ethoxyphenylboronate (136 g, 0.42 mol) in THF (500 mL) was added diluted HCl (2N, 200 mL) slowly at room temperature with stirring. After stirred for 1.5 h at room temperature, the reaction mixture was basified with 20% aqueous solution of NaOH to pH=12 and then washed with EtOAc (2×100 mL). The aqueous layer was acidified by using the diluted HCl (2N) to pH=2 and then extracted with EtOAc (3×100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated to dryness. The residue was purified by column chromatography on silica gel to give the target compound as white solid (80 g, yield 83%). 1H NMR (400 MHz, DMSO-d) δ 9.93 (s, 1H), 7.92 (s, 2H), 7.45-7.48 (m, 2H), 7.23-7.28 (d, 1H), 4.01-4.06 (m, 2H), 1.69-1.20 (m, 3H).

Workup

  1. stirringAfter stirred for 1.5 h at room temperature
  2. washwashed with EtOAc (2×100 mL)
  3. extractionextracted with EtOAc (3×100 mL)
  4. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-94b8a962c542496d8ab121d977ddaa51
Source dataset
uspto-grants-2014_04
Patent number
US08703742B2

Reaction notes

Loading…