Hydrochloric Acid → HCID 18653276, compound

HRID 1109647Notes

Reaction equation

HRID 1109647 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.C(OCC)(=O)C>[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

8

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 24758Sodium hydrideHCID 10966911HCID 10966911, compound

Product 1

HCID 18653276HCID 18653276, compoundYield 46.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

A solution of (R)-3-[1-(5-methoxy-3,4-methylenedioxyphenyl)methyl]butanolide (21.0 g, 0.084 mol) and 3,4,5-trimethoxybenzaldehyde (26.0 g, 0.133 mol) in toluene (350 ml) was cooled to 0° C. under an argon stream, followed by the addition of sodium hydride (60%, 9.1 g, 0.228 mol) and methanol (0.33 ml, 0.0082 mol). After stirred at 0° C. for 15 minutes and then at room temperature for 18 hours, the reaction mixture was ice cooled and then acidified with 2N-HCl. After the addition of ethyl acetate (100 ml), the organic layer was separated. The water layer was extracted with ethyl acetate (50 ml×2). The extracts were combined with the previously-obtained organic layer. The organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl, followed by drying over anhydrous magnesium sulfate. The solvent was distilled off. The residue thus obtained (52.9 g) was purified by column chromatography (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 16.62 g of the title compound were obtained as colorless oil (yield: 46%). [α]27D : -53.7° (C=1.04, CHCl3)

Workup

  1. waitat room temperature for 18 hours
  2. temperaturecooled
  3. customthe organic layer was separated
  4. extractionThe water layer was extracted with ethyl acetate (50 ml×2)
  5. washThe organic layer was washed successively with water, saturated NaHCO3 and saturated NaCl
  6. dry with materialby drying over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customThe residue thus obtained (52.9 g)
  9. 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-d21fc55bd860405db9cf2f8050e93e19
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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