Boron trifluoride etherate → HCID 10690653, compound

HRID 1755950Notes

Reaction equation

HRID 1755950 reaction equation
CO[CH:3]([O:27][CH3:28])[CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH2:13][C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:17][C:18]=3[CH3:19])=[CH:10][C:9]=2[CH:26]=1.C[Si]([C:33]#[N:34])(C)C.B(F)(F)F.CCOCC>ClCCl>[CH3:28][O:27][CH:3]([CH2:4][C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([CH2:13][C:14]3[N:15]=[C:16]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[O:17][C:18]=3[CH3:19])=[CH:10][C:9]=2[CH:26]=1)[C:33]#[N:34]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 82115Trimethylsilyl cyanideHCID 10571637HCID 10571637, compound

Product 1

HCID 10690653HCID 10690653, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(2,2-dimethoxyethyl)-2-[(5-methyl-2-phenyl-4-oxazolyl)methyl]benzofuran (0.75 g, 2.0 mmol) in dichloromethane (15 ml) were added trimethylsilyl cyanide (0.80 ml, 6.0 mmol) and boron trifluoride etherate (50 μl, 0.5 mmol). After 1 hour the solution was diluted with dichloromethane, washed with 5% sodium bicarbonate, water and brine, dried over magnesium sulfate and concentrated. The product was purified by flash-chromatography (hexanes/ethyl acetate, 2:1) and isolated as a solid (0.64 g, mp 107°-109° C.).

Workup

  1. washwashed with 5% sodium bicarbonate, water and brine
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe product was purified by flash-chromatography (hexanes/ethyl acetate, 2:1)

Sources & evidence

ORD record
ord-374c45fa0b56448a9b111d959c542d27
Source dataset
uspto-grants-1995_08
Patent number
US05438074

Reaction notes

Loading…