Boron trifluoride etherate → HCID 23507839, compound

HRID 1377102Notes

Reaction equation

HRID 1377102 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[CH:26]=[CH:25][CH:24]=[C:23]3[C:17]=2[CH2:18][CH2:19][CH:20]2[O:22][CH:21]23)[C:10](=[O:15])[C:11]([F:14])([F:13])[F:12])=[CH:5][CH:4]=1)#[N:2].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>C(OCC)C.C(Cl)Cl>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]([C:16]2[C:17]3[CH2:18][CH2:19][C:20](=[O:22])[CH2:21][C:23]=3[CH:24]=[CH:25][CH:26]=2)[C:10](=[O:15])[C:11]([F:12])([F:14])[F:13])=[CH:5][CH:4]=1)#[N:2]

Participants

6

Reactant 3

HCID 8000Boron trifluoride etherate2×HCID 516892Sodium BicarbonateHCID 23507881HCID 23507881, compound

Product 1

HCID 23507839HCID 23507839, compoundYield 41.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-(4-cyanophenyl)-2,2,2-trifluoro-N-(1a,2,3,7b-tetrahydronaphth[1,2-b]oxiren-4-yl)acetamide (2.8 g, 7.8 mmol) in diethyl ether (80 ml) was treated with BF3.Et2O (2.0 ml, 16 mmol) and the resulting suspension was stirred at room temperature. The suspension was diluted with methylene chloride after 1 and 3 hours (80 and 40 ml) and additional BF3.Et2O (2×1.0 ml, 16 mmol) was added at 2 and 4 hour intervals. The reaction mixture was stirred overnight, then saturated NaHCO3 solution (70 ml) slowly added. The aqueous phase was separated and extracted with methylene chloride (40 ml). The organic solutions were dried (K2CO3), concentrated in vacuo, and the residue purified by chromatography on silica gel with diethyl ether:hexane (2:3 to 1:1) to give N-(4-cyanophenyl)-2,2,2-trifluoro-N-(5,6,7,8-tetrahydro-6-oxo-1-naphthyl)acetamide (1.17 g). 1H NMR (CDCl3, 200 MHz) δ: 2.44 (t, J=7 Hz, 2H, CH2), 2.69 (dt, J=16,7 Hz, 1H, CH2), 3.03 (dt, J=16,6 Hz, 1H, CH2), 3.63 (strongly coupled AB pair, 2H, C5H2), 7.25-7.45 (m, 5H, Ar), 7.67 (d, J=9 Hz, 2H, Ar). Anal. Calculated for C19H13F3N2O2 : C, 63.69; H, 3.66; N, 7.82. Found: C, 63.75; H, 3.72; H, 7.74.

Workup

  1. additionwas added at 2 and 4 hour intervals
  2. stirringThe reaction mixture was stirred overnight
  3. customThe aqueous phase was separated
  4. extractionextracted with methylene chloride (40 ml)
  5. dry with materialThe organic solutions were dried (K2CO3)
  6. concentrationconcentrated in vacuo
  7. customthe residue purified by chromatography on silica gel with diethyl ether:hexane (2:3 to 1:1)

Sources & evidence

ORD record
ord-d63b9a54b43a4b609b5283d7bba60dbf
Source dataset
uspto-grants-1997_09
Patent number
US05663337

Reaction notes

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