Tetrafluoroboric acid → HCID 15840530, compound

HRID 398062Notes

Reaction equation

HRID 398062 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5](N)=[CH:4][C:3]1=2.[H+].[B-](F)(F)(F)[F:23].N([O-])=O.[Na+]>O>[CH3:1][C:2]1([CH3:20])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:5]([F:23])=[CH:4][C:3]1=2

Participants

5

Reactant 3

HCID 28118Tetrafluoroboric acidHCID 15840529HCID 15840529, compound2×HCID 23668193Sodium Nitrite

Product 1

HCID 15840530HCID 15840530, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In an ice bath, ethyl 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-3-aminonaphthalene-2-carboxylate (Compound C, 150 mg, 0.55 mmol) was added 0.24 ml of HBF4 (48% solution in water), followed by a solution of NaNO2 (81 mg, 1.16 mmol) in 1 ml of water. The slurry was left in a refrigerator for 3 days. The reaction mixture was washed successively with ethyl acetate until TLC showed no UV visible spot at the baseline. The ethyl acetate layer was dried with MgSO4 and the solution was concentrated to an oil. The oil was further dissolved in 1 ml of toluene and the mixture was heated under reflux for 2 h. After the reaction cooled to room temperature, solvent was evaporated and the residue was passed through a column (silica gel, ethyl acetate/hexane 1/10) to give the title compound as an oil.

Workup

  1. washThe reaction mixture was washed successively with ethyl acetate until TLC
  2. dry with materialThe ethyl acetate layer was dried with MgSO4
  3. concentrationthe solution was concentrated to an oil
  4. dissolutionThe oil was further dissolved in 1 ml of toluene
  5. temperaturethe mixture was heated
  6. temperatureunder reflux for 2 h
  7. customsolvent was evaporated

Sources & evidence

ORD record
ord-f9069ab9516c47ab99d66506773bd6d8
Source dataset
uspto-grants-2003_08
Patent number
US06610744B2

Reaction notes

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