Ethyl Acetate → HCID 18653280, compound

HRID 1109650Notes

Reaction equation

HRID 1109650 reaction equation
C(=O)([O-])[O-].[K+].[K+].I[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[OH:14][C:15]1[CH:16]=[C:17]([CH2:24][C@@H:25]2[CH2:30][O:29][C:27](=[O:28])/[C:26]/2=[CH:31]/[C:32]2[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=2)[CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[OH:21].C(O[CH2:48][CH3:49])(=O)C>CN(C=O)C>[CH2:8]([O:14][C:15]1[CH:16]=[C:17]([CH2:24][C@@H:25]2[CH2:30][O:29][C:27](=[O:28])/[C:26]/2=[CH:31]/[C:32]2[CH:37]=[C:36]([O:38][CH3:39])[C:35]([O:40][CH3:41])=[C:34]([O:42][CH3:43])[CH:33]=2)[CH:18]=[C:19]([O:22][CH3:23])[C:20]=1[O:21][CH2:8][CH2:9][CH2:10][CH2:11][CH2:48][CH3:49])[CH2:9][CH2:10][CH2:11][CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 125271-IodohexaneHCID 10894986HCID 10894986, compound

Product 1

HCID 18653280HCID 18653280, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (500 mg, 3.6 mmol) and 1-iodohexane (1.0 ml, 6.79 mmol) were added to a solution of (S)-(E)-3-[1-(3,4-dihydroxy-5-methoxyphenyl)methyl]-2-(3,4,5-trimethoxybenzylidene)butanolide (324 mg, 0.78 mmol) in 10 ml of DMF, followed by stirring at 60° C. for 4.5 hours. The reaction mixture was poured into 50 ml of ethyl acetate and then the resulting solution was washed successively with water, 2N-HCl, water and saturated NaHCO3. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure. Brown oil thus obtained was purified by column chromatography (silica gel: "FUJI-DAVIDSON BW-300", eluent: 1:3 mixed solvent of ethyl acetate and hexane), whereby 310 mg of the title compound were obtained as colorless oil (yield: 68%).

Workup

  1. washthe resulting solution was washed successively with water, 2N-HCl, water and saturated NaHCO3
  2. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customBrown oil thus obtained
  5. customwas purified by column chromatography (silica gel: "FUJI-DAVIDSON BW-300", eluent: 1:3 mixed solvent of ethyl acetate and hexane)

Sources & evidence

ORD record
ord-3a9b2d034da1446bad02f3ae86938a84
Source dataset
uspto-grants-1994_06
Patent number
US05321135

Reaction notes

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