Methyl Acrylate → methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate

HRID 322961Notes

Reaction equation

HRID 322961 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH:5]=[CH:6][CH:7]=1.[C:18]([O:22][CH3:23])(=[O:21])[CH:19]=[CH2:20].CC(C)([O-])C.[K+]>O1CCCC1>[I:1][C:2]1[CH:3]=[C:4]([C:8](=[O:17])[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[CH3:16])[CH2:20][CH2:19][C:18]([O:22][CH3:23])=[O:21])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 220101981-(3-Iodophenyl)-2-(2-methylphenyl)ethanoneHCID 23665647Potassium tert-butoxide

Product 1

HCID 54018710methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-iodophenyl)-2-(2-methylphenyl)ethanone (3.21 g) in dry tetrahydrofuran (30 mL) is treated with methyl acrylate (0.9 mL) and potassium tertiary butoxide (0.107 g). The reaction mixture is heated at reflux for 18 hours, evaporated and the residue partitioned between ethyl acetate (60 mL) and water (30 mL). The organic phase is dried over magnesium sulphate, evaporated and the residual solid washed with pentane to give methyl (RS)-5-(3-iodophenyl)-4-(2-methylphenyl)-5-oxopentanoate as a fawn coloured solid (3.39 g), m.p. 106-108° C.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 18 hours
  3. customevaporated
  4. customthe residue partitioned between ethyl acetate (60 mL) and water (30 mL)
  5. dry with materialThe organic phase is dried over magnesium sulphate
  6. customevaporated
  7. washthe residual solid washed with pentane

Sources & evidence

ORD record
ord-671d0db8208e4f7f86bcf4d3aca56add
Source dataset
uspto-grants-2001_04
Patent number
US06211234B1

Reaction notes

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