Boron trifluoride etherate → HCID 18980081, compound

HRID 2392628Notes

Reaction equation

HRID 2392628 reaction equation
[BH4-].[Na+].B(F)(F)F.CCOCC.[C:12]([CH2:14][O:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[O:25][CH3:26])#[N:13].C([O-])(O)=O.[Na+]>C1COCC1>[NH2:13][CH2:12][CH2:14][O:15][C:16]1[CH:21]=[C:20]([N+:22]([O-:24])=[O:23])[CH:19]=[CH:18][C:17]=1[O:25][CH3:26]

Participants

6

Reactant 4

HCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 8946731HCID 8946731, compound

Product 1

HCID 18980081HCID 18980081, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (0.55 g, 0.015 mole) in dry THF (50 ml) at 0° C., under an argon atmosphere, was added boron trifluoride etherate (2.4 ml, 0.02 mole) dropwise. After addition was completed the mixture was left to stir for 1 hour at room temperature and then a solution of 2-cyanomethoxy-4-nitroanisole (D8 1.0 g, 0,0048 mole) in dry THF (50 ml) was added and the mixture heated under reflux for 1 hour. The mixture was treated with saturated aqueous NaHCO3 solution until effervescence had ceased and then concentrated in vacuo. The residue was treated with water and extracted with dichloromethane. The combined organic extracts were dried and concentrated in vacuo to give the title compound (1.0 g, 100%).

Workup

  1. additionAfter addition
  2. waitwas left
  3. temperaturethe mixture heated
  4. temperatureunder reflux for 1 hour
  5. concentrationconcentrated in vacuo
  6. additionThe residue was treated with water
  7. extractionextracted with dichloromethane
  8. customThe combined organic extracts were dried
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-eaa6972b023e4321aa27e91e728f76fe
Source dataset
uspto-grants-1998_09
Patent number
US05801170

Reaction notes

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