Hydrochloric Acid → HCID 11144422, compound

HRID 1109648Notes

Reaction equation

HRID 1109648 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[O:18][CH2:17][O:16][C:5]=2[CH:6]=[C:7]([CH2:9][C@@H:10]2[CH2:15][O:14][C:12](=[O:13])[CH2:11]2)[CH:8]=1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([CH:26]=[C:27]([O:31][CH3:32])[C:28]=1[O:29][CH3:30])[CH:24]=O.[H-].[Na+].CO.Cl>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]2[O:18][CH2:17][O:16][C:5]=2[CH:6]=[C:7]([CH2:9][C@@H:10]2[CH2:15][O:14][C:12](=[O:13])/[C:11]/2=[CH:24]/[C:23]2[CH:26]=[C:27]([O:31][CH3:32])[C:28]([O:29][CH3:30])=[C:21]([O:20][CH3:19])[CH:22]=2)[CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 24758Sodium hydrideHCID 11086167HCID 11086167, compound

Product 1

HCID 11144422HCID 11144422, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (S)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]butanolide (25.0 g, 0.1 mol) and 3,4,5-trimethoxybenzaldehyde (31.0 g, 0.16 mol) in 400 ml of toluene was cooled to 0° C. under an argon stream, followed by the addition of 10.8 g of sodium hydride (60%, 0.27 mol) and 0.4 ml (0.01 mol) of methanol. After stirred at 0° C. for 15 minutes and further at room temperature for 48 hours, the reaction mixture was ice-cooled and added with 100 ml of 6N-HCl. After the removal of the water layer, the organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl, and then dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by column chromatography (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 20.38 g of the title compound were obtained as colorless oil (yield: 48%).

Workup

  1. temperaturecooled
  2. customAfter the removal of the water layer
  3. washthe organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent
  7. customwas purified by column chromatography (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-fde2866a996a4f0a8ff9bddbde569867
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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