3,4,5-Trimethoxybenzaldehyde → HCID 14270146, compound

HRID 1651840Notes

Reaction equation

HRID 1651840 reaction equation
C([Li])CCC.[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[C:10]#[CH:11])[CH3:7].[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[CH:20]=[O:21].[Cl-].[NH4+]>O1CCCC1.CCOCC>[CH2:6]([O:8][CH:9]([O:12][CH2:13][CH3:14])[C:10]#[C:11][C:20]([C:19]1[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:17]([O:16][CH3:15])[CH:18]=1)=[O:21])[CH3:7]

Participants

7

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 25517Ammonium ChlorideHCID 662853,3-DiethoxypropyneHCID 178418339Butyllithium

Product 1

HCID 14270146HCID 14270146, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

43.6 ml of n-butyllithium solution (1.6M in hexane) are added at -78° to a solution of 10 ml (69.8 mmol) of 3,3-diethoxy-1-propyne in 210 ml of absolute tetrahydrofuran. The mixture was stirred at -78° for 30 minutes and treated at -40° with 13.70 g (69.8 mmol) of 3,4,5-trimethoxybenzaldehyde in 60 ml of tetrahydrofuran. The reaction mixture was stirred at 0° for 1 hour and treated with 100 ml of saturated ammonium chloride solution and 150 ml of ether. The aqueous phase was extracted twice with ether. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was dissolved in 100 ml of methylene chloride and added dropwise at 0° to a suspension of 176.8 g of manganese dioxide in 300 ml of methylene chloride. The reaction mixture was stirred at 0° for 20 minutes, filtered over magnesium sulphate and evaporated. The residue was crystallized from iso-octane at 0° and there is obtained 4,4-diethoxy-1-(3,4,5-trimethoxyphenyl)-2-butyn-1-one of melting point 52°-54°.

Workup

  1. stirringThe reaction mixture was stirred at 0° for 1 hour
  2. extractionThe aqueous phase was extracted twice with ether
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customevaporated
  5. dissolutionThe residue was dissolved in 100 ml of methylene chloride
  6. additionadded dropwise at 0° to a suspension of 176.8 g of manganese dioxide in 300 ml of methylene chloride
  7. stirringThe reaction mixture was stirred at 0° for 20 minutes
  8. filtrationfiltered over magnesium sulphate
  9. customevaporated
  10. customThe residue was crystallized from iso-octane at 0°

Sources & evidence

ORD record
ord-e5688756e3e045b285680f9b64c6fd1b
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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