Methyl Ethyl Ketone → HCID 66971623, compound

HRID 1361075Notes

Reaction equation

HRID 1361075 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].[CH2:7](Br)[C:8]1C=CC=[CH:10][CH:9]=1.[CH2:15]([O:19][C:20]1[CH:21]=[C:22]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH:23]=[CH:24][C:25]=1[CH2:26][CH2:27][CH2:28][C:29]1C=CC(O)=C(OC)[CH:30]=1)[CH2:16][CH2:17]C.[CH2:44]([C:46]([CH3:48])=[O:47])[CH3:45]>C(OCC)(=O)C>[CH2:7]([O:47][C:46]1[CH:48]=[CH:30][C:29]([CH2:28][CH2:27][CH2:26][C:25]2[CH:24]=[CH:23][C:22]([CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])=[CH:21][C:20]=2[O:19][CH2:15][CH2:16][CH3:17])=[CH:45][C:44]=1[O:4][CH3:1])[CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 6569Methyl Ethyl KetoneHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 66971962HCID 66971962, compound

Product 1

HCID 66971623HCID 66971623, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.21 g (0.75 mmol) of potassium carbonate and then 0.85 ml (0.75 mmol) of benzyl bromide 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 and then cooled, diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 259 mg (93%) of methyl 3-{4-[3-(4-butoxy-3-methoxyphenyl)propyl]-3-propoxyphenyl}propanoate are obtained in the form of a colorless oil.

Workup

  1. temperaturecooled
  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 purified by chromatography on a column of silica
  7. washeluted with an 80/20 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-c3eb8b27133a48839e87ae4bf85d31b3
Source dataset
uspto-grants-2011_02
Patent number
US07879907B2

Reaction notes

Loading…