Sodium ethoxide → 1-[4'-(4"-Chlorophenyl)phenyl]-3,3-dicarboethoxy-1-oxo-7-phenylheptane

HRID 1419185Notes

Reaction equation

HRID 1419185 reaction equation
[C:1]([CH:6]([CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)=[CH:17][CH:16]=1)=[O:14])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([O:3][CH2:4][CH3:5])=[O:2].[O-]CC.[Na+].[C:32]1([CH2:38][CH2:39][CH2:40][CH2:41]I)[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>COCCOC>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([C:18]2[CH:17]=[CH:16][C:15]([C:13](=[O:14])[CH2:12][C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])([C:1]([O:3][CH2:4][CH3:5])=[O:2])[CH2:41][CH2:40][CH2:39][CH2:38][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:20][CH:19]=2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 2723922Sodium ethoxideHCID 12709818(4-Iodobutyl)benzeneHCID 22116404Ethyl 2-carboethoxy-4[4'-(4"-chlorophenyl)phenyl]-4-oxobutanoate

Product 1

HCID 543714311-[4'-(4"-Chlorophenyl)phenyl]-3,3-dicarboethoxy-1-oxo-7-phenylheptaneYield 56.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

Ethyl 2-carboethoxy-4[4'-(4"-chlorophenyl) phenyl]-4-oxobutanoate (0.40 g, 1.02 mmol) was added in one portion at rt to a solution of sodium ethoxide (0.08 g, 1.12 mmol) in DME (1 mL). After 15 min, 4-phenyl-1-iodobutane (0.24 g, 0.93 mmol) in DME (3 mL) was added. The resulting solution was stirred for 18 h. The solvent was concentrated in vacuo and the resulting oil dissolved in CH2Cl2 (100 mL) and washed with water (100 mL). The phases were separated and the aqueous phase was extracted with CH2Cl2 (2×50 mL). The combined organic phases were dried (MgSO4), filtered, and concentrated in vacuo. The resulting oil was purified by flash chromatography on silica gel using a gradient of ethyl acetate/hexane (10% to 25% ethyl acetate) as the eluent to afford a crystalline solid which was recrystallized with hexane and ethyl acetate to afford 1-[4'-(4"-chlorophenyl)phenyl]-3,3-dicarboethoxy-1-oxo-7-phenylheptane (0.272 g, 28%).

Workup

  1. concentrationThe solvent was concentrated in vacuo
  2. dissolutionthe resulting oil dissolved in CH2Cl2 (100 mL)
  3. washwashed with water (100 mL)
  4. customThe phases were separated
  5. extractionthe aqueous phase was extracted with CH2Cl2 (2×50 mL)
  6. dry with materialThe combined organic phases were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe resulting oil was purified by flash chromatography on silica gel using a gradient of ethyl acetate/hexane (10% to 25% ethyl acetate) as the eluent
  10. customto afford a crystalline solid which
  11. customwas recrystallized with hexane and ethyl acetate

Sources & evidence

ORD record
ord-f016baac018f4c4eb2f69a05796f7b4a
Source dataset
uspto-grants-1999_03
Patent number
US05886024

Reaction notes

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