Hydrochloric Acid → HCID 11004468, compound

HRID 1109644Notes

Reaction equation

HRID 1109644 reaction equation
[H-].[Na+].CO.[CH3:5][O:6][C:7]1[C:8]2[O:22][CH2:21][O:20][C:9]=2[CH:10]=[C:11]([CH2:13][CH:14]2[CH2:19][O:18][C:16](=[O:17])[CH2:15]2)[CH:12]=1.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([CH:30]=[C:31]([O:35][CH3:36])[C:32]=1[O:33][CH3:34])[CH:28]=O.Cl>C(OCC)(=O)C.O.C1(C)C=CC=CC=1>[CH3:5][O:6][C:7]1[C:8]2[O:22][CH2:21][O:20][C:9]=2[CH:10]=[C:11]([CH2:13][CH:14]2[CH2:19][O:18][C:16](=[O:17])/[C:15]/2=[CH:28]/[C:27]2[CH:30]=[C:31]([O:35][CH3:36])[C:32]([O:33][CH3:34])=[C:25]([O:24][CH3:23])[CH:26]=2)[CH:12]=1

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 24758Sodium hydrideHCID 19020972HCID 19020972, compound

Product 1

HCID 11004468HCID 11004468, compoundYield 42.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (60%, 0.43 g, 10.8 mmol) and methanol (0.016 ml, 0.4 mmol) were added to 20 ml of toluene under an argon stream. The solution was added further with (RS)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]butanolide [1.0 g, 4 mmol, G. E. Schneiders and R. Stevenson, J. Chem. Soc. Perkin I, 999, (1982)] and 3,4,5-trimethoxybenzaldehyde (1.24 g, 6.3 mol), followed by stirring at room temperature for 24 hours. The reaction mixture was added with 2N-HCl. The solution was dissolved in ethyl acetate, from which the water layer was removed. The organic layer was washed with saturated NaCl and then, dried over anhydrous magnesium sulfate. The solvent was distilled off. The residue thus obtained was purified by column chromatography (silica gel: "MERCK #9385", 50 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 732 mg of the title compound were obtained as a colorless solid (yield: 43%).

Workup

  1. customwas removed
  2. washThe organic layer was washed with saturated NaCl
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customThe residue thus obtained
  6. customwas purified by column chromatography (silica gel: "MERCK #9385", 50 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-3539614b9e4d46aabfa0a370d1951b68
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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