4-Methoxybenzaldehyde → 1'-Hydroxyestragole

HRID 706361Notes

Reaction equation

HRID 706361 reaction equation
[CH:1](=[O:10])[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[CH:11]([Mg]Br)=[CH2:12]>O1CCCC1>[CH3:9][O:8][C:5]1[CH:6]=[CH:7][C:2]([CH:1]([OH:10])[CH:11]=[CH2:12])=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 312444-MethoxybenzaldehydeHCID 178418507HCID 178418507, compound

Product 1

HCID 400031'-HydroxyestragoleYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of p-anisaldehyde (1.54 ml) in tetrahydrofuran (20 ml) at −10° C. under argon was added dropwise vinyl magnesium bromide (1 M in THF, 12.5 ml). The solution was stirred overnight at room temperature and quenched by addition of saturated aqueous ammonium chloride (20 ml). The organic phase was separated, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (SiO2, ethyl acetate:cyclohexan 7:3) to give 1.05 g of the desired product as a colorless oil (51%) which was characterized by its mass and NMR spectra.

Workup

  1. customquenched by addition of saturated aqueous ammonium chloride (20 ml)
  2. customThe organic phase was separated
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (SiO2, ethyl acetate:cyclohexan 7:3)

Sources & evidence

ORD record
ord-641178c6b4c342fa8bdd06a762266edc
Source dataset
uspto-grants-2015_11
Patent number
US09174987B2

Reaction notes

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