3,4,5-Trimethoxybenzaldehyde → 1-(3,4,5-Trimethoxyphenyl)-2-propyn-1-ol

HRID 273343Notes

Reaction equation

HRID 273343 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([O:13][CH3:14])[C:10]=1[O:11][CH3:12])[CH:6]=[O:7].[C-:15]#[C-:16].[Na+].[Na+]>C1COCC1>[CH3:14][O:13][C:9]1[CH:8]=[C:5]([CH:6]([OH:7])[C:15]#[CH:16])[CH:4]=[C:3]([O:2][CH3:1])[C:10]=1[O:11][CH3:12]

Participants

4

Reactant 2

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 178463197HCID 178463197, compound

Product 1

HCID 161103271-(3,4,5-Trimethoxyphenyl)-2-propyn-1-olYield 73.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 3,4,5-trimethoxybenzaldehyde (1.0 g, 5.0 mmol) in THF (50 mL) was stirred at 0° C. Sodium acetylide (18% w.t. slurry in xylene, 1.63 g, 6.1 mmol) was added via syringe. The reaction mixture was stirred overnight at room temperature and quenched by water. It was then extracted with EtOAc (30 mL×3). The combined organic layers were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give a crude product, which was purified by flash column chromatography eluting with EtOAc/n-hexane (1:2) to afford 1-(3,4,5-trimethoxyphenyl)prop-2-yn-1-ol as a white solid (815 mg, 72%).

Workup

  1. customquenched by water
  2. extractionIt was then extracted with EtOAc (30 mL×3)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas purified by flash column chromatography
  9. washeluting with EtOAc/n-hexane (1:2)

Sources & evidence

ORD record
ord-706fa45e5dde4051bca2c44091994724
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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