Boron trifluoride etherate → HCID 14290027, compound

HRID 2361624Notes

Reaction equation

HRID 2361624 reaction equation
[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9]O)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].[I-:13].[Cs+].B(F)(F)F.CCOCC>C(#N)C>[C:1]([O:4][C:5]1[CH:12]=[CH:11][C:8]([CH2:9][I:13])=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 24601Cesium iodideHCID 959064-Acetoxybenzyl alcohol

Product 1

HCID 14290027HCID 14290027, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

To a solution of 4-acetoxybenzyl alcohol (0.332 g, 2 mmol), and cesium iodide (0.571 g, 2.2 mmol) in anhyd. acetonitrile (10 mL) under nitrogen, boron trifluoride etherate (0.28 mL, 2.2 mmol) in acetonitrile (5 mL) was introduced. After stirring overnight, the reaction mixture was poured into ice-cold water (20 mL) and the solid separated was filtered, washed with water and later with hexanes. The product was dried under high vacuum. Yield, 0.39 g, 71%; TLC, hexanes:EtOAC (4:1). 1H NMR (CDCl3): δ 2.3 (s, 3H), 4.35 (s, 2H), 7.05 (d, 2H), 7.5 (d, 2H).

Workup

  1. customthe solid separated
  2. filtrationwas filtered
  3. washwashed with water and later with hexanes
  4. customThe product was dried under high vacuum
  5. customYield

Sources & evidence

ORD record
ord-3edb94b50cbd40e3bd2bab775639229c
Source dataset
uspto-grants-2014_04
Patent number
US08691787B2

Reaction notes

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