Hydrochloric Acid → HCID 68646048, compound

HRID 1160061Notes

Reaction equation

HRID 1160061 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-dbf75a463f90442cada0b9b1ce9b5a67
Source dataset
uspto-grants-2010_10
Patent number
US07816344B2

Reaction notes

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