Hydrochloric Acid → HCID 11762049, compound

HRID 1109646Notes

Reaction equation

HRID 1109646 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:13][C@H:14]2[CH2:19][O:18][C:16](=[O:17])[CH2:15]2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31])[CH:25]=O.[H-].[Na+].CO.Cl>C1(C)C=CC=CC=1>[CH3:33][O:32][C:28]1[CH:27]=[C:24]([CH:23]=[C:22]([O:21][CH3:20])[C:29]=1[O:30][CH3:31])/[CH:25]=[C:15]1/[C:16]([O:18][CH2:19][C@@H:14]/1[CH2:13][C:5]1[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:17]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 887MethanolHCID 68583,4,5-TrimethoxybenzaldehydeHCID 24758Sodium hydrideHCID 10978386HCID 10978386, compound

Product 1

HCID 11762049HCID 11762049, compoundYield 32.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of (R)-3-[1-(3,4,5-trimethoxyphenyl)-methyl]butanolide [10.52 g, 0.04 mol; K. Lalami, D. Dhai, and E. Brown, Heterocycles, 27, 1131 (1988)] and 3,4,5-trimethoxybenzaldehyde (11.4 g, 0.058 mol) in toluene (150 ml) was cooled to 0° C. under an argon stream. The solution was added with 4.0 g of sodium hydride (60%, 0.1 mol) and 0.15 ml (0.0037 mol) of methanol, followed by stirring at room temperature for 45 hours. The reaction mixture was ice-cooled and then added with 100 ml of 2N-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 solvent was distilled off. The residue thus obtained (20 g) was purified by column chromatography on a silica gel column (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane), whereby 5.71 g of the title compound were obtained as pale yellow oil (yield: 33%). [α]27D : -75.64° (C=0.55, CHCl3)

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. distillationThe solvent was distilled off
  6. customThe residue thus obtained (20 g)
  7. customwas purified by column chromatography on a silica gel column (silica gel: "MERCK #9385", 500 g, eluent: 1:2 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-70d305da90854856ab6792f8ac12765d
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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