Benzaldehyde → alpha-[(2-Furanyl)ethynyl]-benzenemethanol

HRID 1588728Notes

Reaction equation

HRID 1588728 reaction equation
C[Si](C)(C)N[Si](C)(C)C.[Li].[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]#[CH:17].[CH:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCCC1>[O:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]#[C:17][CH:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[OH:25]

Participants

5

Reactant 3

HCID 240BenzaldehydeHCID 140409Furan, 2-ethynyl-HCID 57426343Lithium bis(trimethylsilyl)amide

Product 1

HCID 20076917alpha-[(2-Furanyl)ethynyl]-benzenemethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Place lithium hexamethyldisilazane (3 mL of a 1M solution in tetrahydrofuran, 3 mmol) under argon atmosphere and cool to 0° C. Add 2-furanylacetylene (276 mg, 3 mmol) in tetrahydrofuran (20 mL) and stir at 0° C. until anion formation is complete. Add a solution of benzaldehyde (297 mg, 2.8 mmol) in tetrahydrofuran, remove the ice bath and stir at room temperature until the reaction is complete. Pour onto ethyl ether and water, separate the organic layer and dry (MgSO4). Filter and evaporate the solvent in vacuo. Purify by silica gel chromatography to yield the title compound.

Workup

  1. customremove the ice bath
  2. additionPour onto ethyl ether and water
  3. customseparate the organic layer
  4. dry with materialdry (MgSO4)
  5. filtrationFilter
  6. customevaporate the solvent in vacuo
  7. customPurify by silica gel chromatography

Sources & evidence

ORD record
ord-1347d70d4fcc45bba0b36a1a19f78916
Source dataset
uspto-grants-1993_06
Patent number
US05223518

Reaction notes

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