Iodoethane → HCID 66971978, compound

HRID 1361073Notes

Reaction equation

HRID 1361073 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].I[CH2:8][CH3:9].[CH2:10]([O:14][C:15]1[CH:16]=[C:17]([CH2:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])[CH:18]=[CH:19][C:20]=1[CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[C:26]([O:31][CH3:32])[CH:25]=1)[CH2:11][CH2:12][CH3:13]>C(C(C)=O)C.C(OCC)(=O)C>[CH2:8]([O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][CH2:22][CH2:21][C:20]2[CH:19]=[CH:18][C:17]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:1])=[O:36])=[CH:16][C:15]=2[O:14][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:25][C:26]=1[O:31][CH3:32])[CH3:9]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 66971962HCID 66971962, compound

Product 1

HCID 66971978HCID 66971978, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 6569Methyl Ethyl KetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.21 g (0.75 mmol) of potassium carbonate and then 0.12 ml (0.75 mmol) of iodoethane are added to a solution of 0.25 g (0.62 mmol) of methyl 3-{3-butoxy-4-[3-(4-hydroxy-3-methoxyphenyl)propyl]phenyl}propanoate (prepared according to Example 1d) in 25 ml of methyl ethyl ketone. The reaction mixture is heated at 70° C. for 24 hours. The reaction medium is cooled, diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and evaporated and the residue is then purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 240 mg (93%) of ethyl 3-{4-[3-(4-ethoxy-3-methoxyphenyl)propyl]-3-butoxyphenyl}propanoate are obtained in the form of a colorless oil.

Workup

  1. temperatureThe reaction medium is cooled
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customthe residue is then purified by chromatography on a column of silica
  7. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-a5fb9cd92ebd43c088dbdf0b2ffa23c3
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

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