Hydrochloric Acid → HCID 57451848, compound

HRID 339635Notes

Reaction equation

HRID 339635 reaction equation
[OH-].[Na+].[CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[B:11]([OH:13])[OH:12])=O.[N+:14]([CH2:17][CH3:18])([O-:16])=[O:15].Cl>O.CCOC(C)=O>[N+:14]([CH:17]([CH:3]1[O:13][B:11]([OH:12])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]1=2)[CH3:18])([O-:16])=[O:15]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6587NitroethaneHCID 14798Sodium HydroxideHCID 2921892-Formylphenylboronic acid

Product 1

HCID 57451848HCID 57451848, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of NaOH (1.6 g, 41 mmol) in H2O (20 mL) was added to 2-formyl phenylboronic acid (5.1 g, 34 mmol) at rt. The mixture was stirred for 15 min then nitroethane (2.9 mL, 41 mmol) was added dropwise. The mixture was stirred for 30 min and then the clear reaction solution was acidified with 2 N HCl and EtOAc was added. The organic layer was separated, washed with H2O then brine, dried (Na2SO4), and concentrated in vacuo. Purification by flash chromatography (2:1 hexane/EtOAc) gave the title compound as a colorless oil: yield 6.72 g (quantitative).

Workup

  1. stirringThe mixture was stirred for 30 min
  2. additionwas added
  3. customThe organic layer was separated
  4. washwashed with H2O
  5. dry with materialbrine, dried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (2:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-f776f303307b4a598b47095e091074e6
Source dataset
uspto-grants-2014_11
Patent number
US08895534B2

Reaction notes

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