3,4,5-Trimethoxybenzaldehyde → HCID 12193793, compound

HRID 1651841Notes

Reaction equation

HRID 1651841 reaction equation
C([Li])CCC.[C:6]([O:10][CH2:11][CH3:12])(=[O:9])[C:7]#[CH:8].[CH3:13][O:14][C:15]1[CH:16]=[C:17]([CH:20]=[C:21]([O:25][CH3:26])[C:22]=1[O:23][CH3:24])[CH:18]=[O:19].[Cl-].[NH4+]>O1CCCC1.CCOCC.CCCCCC.O1CCCC1.C(OCC)(=O)C>[OH:19][CH:18]([C:17]1[CH:20]=[C:21]([O:25][CH3:26])[C:22]([O:23][CH3:24])=[C:15]([O:14][CH3:13])[CH:16]=1)[C:8]#[C:7][C:6]([O:10][CH2:11][CH3:12])=[O:9]

Participants

8

Reactant 4

HCID 68583,4,5-TrimethoxybenzaldehydeHCID 12182Ethyl propiolateHCID 25517Ammonium ChlorideHCID 178418339Butyllithium

Product 1

HCID 12193793HCID 12193793, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 21398309HCID 21398309, compoundSolvent

Procedure

72 ml of n-butyllithium solution (1.6M in hexane) were added at -110° to a solution of 11.72 ml (0.115 mol) of ethyl propiolate in 195 ml of tetrahydrofuran/ether/hexane (4:2:1). The mixture was stirred at -110° for 20 minutes and then treated with 15.0 g (76.4 mmol) of 3,4,5-trimethoxybenzaldehyde in 30 ml of tetrahydrofuran. The mixture was thereafter stirred at -78° for 1.5 hours and treated at -30° with 100 ml of saturated ammonium chloride solution and 100 ml of ethyl acetate. The aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over magnesium sulphate and evaporated. The residue was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:1), whereafter there was obtained ethyl 4-hydroxy-4-(3,4,5-trimethoxyphenyl)-2-butynoate.

Workup

  1. stirringThe mixture was thereafter stirred at -78° for 1.5 hours
  2. extractionThe aqueous phase was extracted twice with ethyl acetate
  3. dry with materialThe combined organic phases were dried over magnesium sulphate
  4. customevaporated
  5. customThe residue was chromatographed on 500 g of silica gel with ethyl acetate/hexane (1:1), whereafter there

Sources & evidence

ORD record
ord-7aa1788849a74d92afce1498a3fe8c63
Source dataset
uspto-grants-1990_05
Patent number
US04929741

Reaction notes

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