Potassium Carbonate → 2Z-Ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester

HRID 479157Notes

Reaction equation

HRID 479157 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15][C:16]1[C:24]2[CH2:23][CH2:22][CH2:21][C:20]=2[C:19](C=O)=[CH:18][CH:17]=1.[Cl-].[CH2:28]([O:30][CH:31]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[C:32]([O:34][CH2:35][CH3:36])=[O:33])[CH3:29].[C:56](=O)([O-])[O-].[K+].[K+]>ClCCl.CC(O)C>[CH2:35]([O:34][C:32](=[O:33])/[C:31](/[O:30][CH2:28][CH3:29])=[CH:56]/[C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[C:24]2[C:20]=1[CH2:21][CH2:22][CH2:23]2)[CH3:36]

Participants

5

Reactant 3

HCID 11430Potassium Carbonate3×HCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)3×HCID 180034787-[2-(5-Methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-carbaldehyde

Product 1

HCID 695569192Z-Ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 21966342Isopropanol methylene chlorideSolvent

Conditions

Temperature
-10 °C

Procedure

1.39 g of 7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-carbaldehyde (4.00 mmol) and 1.89 g of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride [Tetrahedron 50(25), 7543-56(1994)] (4.40 mmol) were dissolved in 9 ml of dichloromethane/2-propanol (1/1, v/v) under argon. This solution was cooled down to −10° C. and 855 mg of potassium carbonate (6.00 mmol) was added. The resulting suspension was stirred overnight and allowed to reach room temperature. Additional 1.89 g of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (4.40 mmol) were added, the solution was cooled down to −10° C. and 855 mg of potassium carbonate (6.00 mmol) were added. The resulting suspension was stirred for 60 hours and allowed to reach room temperature. Again, 1.89 g of (ethoxy-ethoxycarbonyl-methyl)-triphenyl-phosphonium chloride (4.40 mmol) were added, the solution was cooled down to −10° C. and 855 mg of potassium carbonate (6.00 mmol) were added. The resulting suspension was stirred overnight and allowed to reach room temperature. The mixture was filtered, washed with dichloromethane and the filtrate evaporated. The residue was dissolved in dichloromethane and washed with brine. Drying over magnesium sulfate, and evaporation of the solvents, followed by flash chromatography (silica gel, cyclohexane, then cyclohexane/ethylacetate=95/5, then cyclohexane/ethylacetate=4/1) left finally 1.215 g (65.8%) of 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester as beige crystals.

Workup

  1. customto reach room temperature
  2. temperaturethe solution was cooled down to −10° C.
  3. stirringThe resulting suspension was stirred for 60 hours
  4. customto reach room temperature
  5. temperaturethe solution was cooled down to −10° C.
  6. stirringThe resulting suspension was stirred overnight
  7. customto reach room temperature
  8. filtrationThe mixture was filtered
  9. washwashed with dichloromethane
  10. customthe filtrate evaporated
  11. dissolutionThe residue was dissolved in dichloromethane
  12. washwashed with brine
  13. dry with materialDrying over magnesium sulfate, and evaporation of the solvents
  14. waitcyclohexane/ethylacetate=95/5, then cyclohexane/ethylacetate=4/1) left finally 1.215 g (65.8%) of 2Z-ethoxy-3-{7-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-indan-4-yl}-acrylic acid ethyl ester as beige crystals

Sources & evidence

ORD record
ord-45c600c53b1148cd89278a10fc8f8a38
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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