5-Fluoro-2-methoxybenzaldehyde → 1-(5-Fluoro-2-methoxy-phenyl)-3-phenyl-prop-2-yn-1-ol

HRID 1037154Notes

Reaction equation

HRID 1037154 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:9]=1)[CH:7]=[O:8].[C:12]1([C:18]#[C:19][Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH:7]([OH:8])[C:19]#[C:18][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 27349435-Fluoro-2-methoxybenzaldehydeHCID 178419644HCID 178419644, compound

Product 1

HCID 670676721-(5-Fluoro-2-methoxy-phenyl)-3-phenyl-prop-2-yn-1-olYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-fluoro-2-methoxybenzaldehyde (933 mg, 6.05 mmol) in anhydrous THF (15 mL) at 0° C. was added phenylethynyl magnesium bromide solution (1M in THF, 9.0 mL, 9.08 mmol). The temperature was allowed to increase to RT over the course of the reaction. After 18 h, the reaction mixture was quenched with saturated aqueous ammonium chloride solution and extracted with EtOAc (20 mL). The organic extracts were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. The resultant residue was subjected to flash chromatography (SiO2, gradient 0 to 30% EtOAc in cyclohexane) to afford the title compound (1.19 g, 77%). 1H NMR (400 MHz, DMSO-d6): δ 7.42-7.32 (m, 6H), 7.16-7.09 (m, 1H), 7.06-7.02 (m, 1H), 6.16-6.13 (d, 1H), 5.78-5.75 (d, 1H), 3.83 (s, 3H).

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride solution
  2. extractionextracted with EtOAc (20 mL)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ff39159ea6e94693ad3e9a58c7d6d449
Source dataset
uspto-grants-2013_10
Patent number
US08546376B2

Reaction notes

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