Ethyl Acetate → HCID 58910060, compound

HRID 1296023Notes

Reaction equation

HRID 1296023 reaction equation
C([Sn](CCCC)(CCCC)[C:6]([O:8]CC)=[CH2:7])CCC.Br[C:20]1[CH:21]=[C:22]([O:34][CH2:35][CH3:36])[C:23]([O:30]COC)=[C:24]([C:26]([CH3:29])([CH3:28])[CH3:27])[CH:25]=1.C(OCC)(=O)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:26]([C:24]1[CH:25]=[C:20]([C:6](=[O:8])[CH3:7])[CH:21]=[C:22]([O:34][CH2:35][CH3:36])[C:23]=1[OH:30])([CH3:27])([CH3:28])[CH3:29]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 22929833HCID 22929833, compound

Product 1

HCID 58910060HCID 58910060, compoundYield 65.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Tributyl(1-ethoxyvinyl)tin (7.77 g, 21.52 mmol) and Pd(PPh3)4 (1.18 g, 1.02 mmol) were added to a solution of the 5-bromo-1-(tert-butyl)-3-ethoxy-2-(methoxymethoxy)benzene (6.5 g, 20.4 mmol) in toluene (68 ml) and the mixture was stirred at 100° C. for 18 hours. The reaction mixture was cooled to room temperature, ethyl acetate was added, the mixture was washed with 20% aqueous KF and filtered through celite, and the organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. A 1 N HCl aqueous solution (15 ml) was added to a solution of the residue in methanol (80 ml), and the mixture was stirred at room temperature for 2 hours. Saturated sodium hydrogencarbonate solution was added to be basic and extraction was performed with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (3.17 g) as colorless crystals.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washthe mixture was washed with 20% aqueous KF
  3. filtrationfiltered through celite
  4. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionA 1 N HCl aqueous solution (15 ml) was added to a solution of the residue in methanol (80 ml)
  7. stirringthe mixture was stirred at room temperature for 2 hours
  8. additionSaturated sodium hydrogencarbonate solution was added
  9. extractionextraction
  10. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f4728fdd5d8f40fa82e24ebba97c00d1
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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