Ethyl Acetate → HCID 57297845, compound

HRID 1598415Notes

Reaction equation

HRID 1598415 reaction equation
CO[CH:3]=[CH:4][C:5]([O:7][Si](C)(C)C)=[CH2:6].[O:12]=[C:13]1[C:22]2[CH2:21][CH:20]([C:23]([CH3:25])=[O:24])[O:19][CH2:18][C:17]=2[C:16](=[O:26])[CH:15]=[CH:14]1.C(OCC)(=O)C>C1(C)C=CC=CC=1>[OH:7][C:5]1[CH:6]=[C:14]2[C:15](=[CH:3][CH:4]=1)[C:16](=[O:26])[C:17]1[CH2:18][O:19][CH:20]([C:23]([CH3:25])=[O:24])[CH2:21][C:22]=1[C:13]2=[O:12]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 11030982HCID 11030982, compound

Product 1

HCID 57297845HCID 57297845, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 1-methoxy-3-trimethylsilyloxy butadiene (776 mg, 4.51 mmol) and methyl (5,8-dioxo-3,4,5,8-tetrahydrobenzo [2,3-C] pyran-3-yl) ketone (309 mg, 1.50 mmol) in 6 mL of dry toluene was stirred for 90 minutes at room temperature under argon atmosphere. The solvent was then removed in vacuo and the dried residue was dissolved in 10 mL of THF. To this solution was added 2 mL of a 4% aq. HCl solution. The combined organic layers were then washed with water and dried over MgSO4. Flash chromatography (toluene:ethyl acetate; 95%:5%) of the residue gave 180 mg (65% yield) of the titled compound (MP: 169°-170° C.).

Workup

  1. customThe solvent was then removed in vacuo
  2. dissolutionthe dried residue was dissolved in 10 mL of THF
  3. additionTo this solution was added 2 mL of a 4% aq. HCl solution
  4. washThe combined organic layers were then washed with water
  5. dry with materialdried over MgSO4

Sources & evidence

ORD record
ord-42c7e44973e14f48b9d0ff3b559b50c9
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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