Water → HCID 70223406, compound

HRID 1384159Notes

Reaction equation

HRID 1384159 reaction equation
I[C:2]1[CH:3]=[C:4]([C:8]([C:10]2[CH:19]=[CH:18][C:17]3[C:16]([CH3:21])([CH3:20])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]=3[CH:11]=2)=[O:9])[CH:5]=[CH:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:34][CH3:35])(=[O:33])[CH:31]=[CH2:32].O>CN(C=O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:20][C:16]1([CH3:21])[CH2:15][CH2:14][C:13]([CH3:23])([CH3:22])[C:12]2[CH:11]=[C:10]([C:8]([C:4]3[CH:3]=[C:2]([CH:32]=[CH:31][C:30]([O:34][CH3:35])=[O:33])[CH:7]=[CH:6][CH:5]=3)=[O:9])[CH:19]=[CH:18][C:17]1=2

Participants

8

Reactant 4

HCID 962WaterHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 15428931HCID 15428931, compound

Product 1

HCID 70223406HCID 70223406, compound

Reagents, catalysts & solvents 3

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of 2 g (4.8 mmol) of 3-iodophenyl-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydro-2-naphthyl)-methanone in 30 ml of DMF is introduced into a three-necked flask under a stream of nitrogen, followed by successive addition of 1.7 g of potassium carbonate, 1.4 g of tetrabutylammonium chloride and 600 μl (6.2 mmol) of methyl acrylate. The reaction medium is degassed by bubbling a stream of argon through it, and 22 mg (0.1 mmol) of palladium acetate are introduced. The reaction medium is heated at 55° C. for six hours and then poured into water, the mixture is extracted with ethyl acetate and the organic phase is separated out after settling has taken place, washed with water, dried over magnesium sulphate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of ethyl acetate and heptane (90/10). After evaporation of the solvents, 1.39 g (77%) of the expected methyl ester, with a melting point of 103-4° C., are collected.

Workup

  1. customThe reaction medium is degassed
  2. additionare introduced
  3. extractionthe mixture is extracted with ethyl acetate
  4. customthe organic phase is separated out after settling
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. customevaporated
  8. customThe residue obtained
  9. customis purified by chromatography on a column of silica
  10. washeluted with a mixture of ethyl acetate and heptane (90/10)
  11. customAfter evaporation of the solvents, 1.39 g (77%) of the expected methyl ester
  12. customwith a melting point of 103-4° C., are collected

Sources & evidence

ORD record
ord-6632822968f94db2a8b4846c5d410bf3
Source dataset
uspto-grants-2001_07
Patent number
US06258775B1

Reaction notes

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