3,4,5-Trimethoxybenzaldehyde → HCID 23050445, compound

HRID 1651802Notes

Reaction equation

HRID 1651802 reaction equation
C([Li])CCC.[C:6]([O:10][CH3:11])(=[O:9])[C:7]#[CH:8].[CH3:12][O:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH:17]=[O:18].[Cl-].[NH4+]>O1CCCC1.CCOCC.CCCCCC.CCOCC>[OH:18][CH:17]([C:16]1[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([O:13][CH3:12])[CH:15]=1)[C:8]#[C:7][C:6]([O:10][CH3:11])=[O:9]

Participants

7

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 13536Methyl propiolateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 23050445HCID 23050445, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21398309HCID 21398309, compoundSolvent

Procedure

71.6 ml of n-butyllithium solution (1.6M in hexane) were added to a solution of 9.6 ml (0.115 mol) of methyl propiolate in 195 ml of tetrahydrofuran/ether/hexane (4:2:1) at -110° . The mixture was stirred at -110° for 20 minutes, whereupon 15.0 g (76.4 mmol) of 3,4,5 -trimethoxybenzaldehyde in 15 ml of ether were added within 20 minutes. The reaction mixture was stirred at -78° for a further 90 minutes, then brought slowly to room temperature and thereupon treated with 100 ml of saturated ammonium chloride solution. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. Chromatography on silica gel with ethyl acetate/hexane (1:2) yielded methyl 4-hydroxy-4-(3,4,5 -trimethoxyphenyl)-2-butynoate.

Workup

  1. additionwere added within 20 minutes
  2. custombrought slowly to room temperature
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. customevaporated

Sources & evidence

ORD record
ord-a0407767e46149eea7d1b31aea9330f3
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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