Boron trifluoride → HCID 18624266, compound

HRID 1860626Notes

Reaction equation

HRID 1860626 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2(O)[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2].C[Si]([C:24]#[N:25])(C)C.B(F)(F)F.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2([C:24]#[N:25])[CH:16]3[CH2:17][CH:12]4[CH2:13][CH:14]([CH2:18][CH:10]2[CH2:11]4)[CH2:15]3)[CH:6]=[CH:7][CH:8]=1)[CH3:2]

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 18624262HCID 18624262, compound

Product 1

HCID 18624266HCID 18624266, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2-(3-ethylphenyl)-2-adamantanol (1.82 g, 7.14 mmol) in dry CHCl3 (5 mL) under argon, was treated with trimethylsilyl cyanide (1.00 mL, 7.5 mmol), cooled to 0° C., treated with BF3 etherate (1.10 mL, 8.57 mmol), allowed to warm to room temperature and stirred for 2 h. The mixture was treated with dilute NaHCO3 (10 mL), extracted with CHCl3 (2×10 mL), the combined extracts washed with water (10 mL), dried (MgSO4), concentrated in vacuo and purified by chromatography [SiO2; heptane-EtOAc (9:1)] to give the product (1.54 g, 82%) as a colourless oil: IR νmax (thin film)/cm−1 2922, 2860, 2226, 1604, 1487, 1453, 1105, 799 and 704; NMR δH (400 MHz, CDCl3) 1.24 (3H, t, J 7.5 Hz), 1.62-1.65 (2H, m), 1.70-1.82 (5H, m), 1.98-204 (3H, m), 2.45-2.48 (2H, m), 2.66 (2H, q, J 7.5 Hz), 2.79 (2H, s), 7.15 (1H, d, J 7.5 Hz) and 7.25-7.34 (3H, m); Anal. Calcd for C19H23N: C, 85.99; H, 8.73; N, 5.28. Found: C, 85.85; H, 8.77; N, 5.23.

Workup

  1. temperatureto warm to room temperature
  2. extractionextracted with CHCl3 (2×10 mL)
  3. washthe combined extracts washed with water (10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. custompurified by chromatography [SiO2; heptane-EtOAc (9:1)]

Sources & evidence

ORD record
ord-cde2e1f205264a15b1ab816767dd6625
Source dataset
uspto-grants-2003_03
Patent number
US06531511B1

Reaction notes

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