Hydrochloric Acid → HCID 68646048, compound

HRID 339613Notes

Reaction equation

HRID 339613 reaction equation
[CH3:1][N+:2]([O-:4])=[O:3].[CH3:5][O:6][C:7](=[O:28])[CH2:8][CH2:9][CH2:10][O:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14](C=O)[C:13]=1[B:20]1[O:25][CH2:24]C(C)(C)C[O:21]1.[OH-].[Na+].Cl.[CH3:32]C#N>O>[CH2:5]([O:6][C:7](=[O:28])[CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:13]2[B:20]([OH:21])[O:25][CH:24]([CH2:1][N+:2]([O-:4])=[O:3])[C:14]=2[CH:15]=[CH:16][CH:17]=1)[CH3:32]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6342AcetonitrileHCID 6375NitromethaneHCID 14798Sodium HydroxideHCID 87528820HCID 87528820, compound

Product 1

HCID 68646048HCID 68646048, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

MeNO2 (1.3 mL, 25 mmol) was added dropwise to a stirred solution of crude 4-[2-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-3-formyl-phenoxy]-butyric acid methyl ester (9.4 g), NaOH (1.0 g, 25 mmol) and H2O (35 mL) in MeCN (90 mL) at rt. The mixture was stirred at rt O/N and then acidified (pH 2) using 4 M HCl. The THF was removed in vacuo and the aqueous layer was extracted with EtOAc. The organic layer was washed with brine, dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (10% to 30% EtOAc in hexane) to give the title compound as a yellow oil: yield 2.52 g (45% over 2 steps).

Workup

  1. customThe THF was removed in vacuo
  2. extractionthe aqueous layer was extracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (10% to 30% EtOAc in hexane)

Sources & evidence

ORD record
ord-977711d46dc04f47bf44489ddede8c43
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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