1-Bromopentane → HCID 53788979, compound

HRID 1603941Notes

Reaction equation

HRID 1603941 reaction equation
[H-].[Na+].[CH2:3](Br)[CH2:4][CH2:5][CH2:6][CH3:7].[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=O)=[CH:13][C:12]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[C:28]([O:31][CH2:32][CH3:33])(=[O:30])[CH3:29]>COCCOC.O>[CH3:9][O:10][C:11]1[CH:18]=[CH:17][C:14]([CH:15]=[C:29]([CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:28]([O:31][CH2:32][CH3:33])=[O:30])=[CH:13][C:12]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 80571-BromopentaneHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 217163814-Methoxy-3-(2-phenylethoxy)benzaldehyde

Product 1

HCID 53788979HCID 53788979, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a suspension of 60% sodium hydride (oily)(0.847 mg) in 25 ml of 1,2-dimethoxyethane, 4.20 ml of triethyl phosphonoacetate was added dropwise over 10 minutes and stirred at room temperature for 1 hour. To this reaction solution, 2.65 ml of pentyl bromide was added, and then refluxed by heating for 3 hours under stirring. Thereafter, the reaction solution was cooled to room temperature and 0.857 mg of 60% sodium hydride (oily) was added thereto. After stirring at room temperature for 30 minutes, 5.15 g of 4-methoxy-3-(2-phenylethoxy)-benzaldehyde was added and refluxed by heating for 2 hours under stirring. Then, the reaction solution was cooled to room temperature, and ethyl acetate and water was added thereto to separate the solution into layers. The organic layer separated was washed with water, an aqueous solution of saturated sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and then the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=30:1) to thereby obtain 5.39 g of ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-pentylacrylate as a mixture of E- and Z-isomers (E-isomer:Z-isomer=7.0:1).

Workup

  1. additionwas added dropwise over 10 minutes
  2. temperaturerefluxed
  3. temperatureby heating for 3 hours
  4. stirringunder stirring
  5. temperatureThereafter, the reaction solution was cooled to room temperature
  6. stirringAfter stirring at room temperature for 30 minutes
  7. temperaturerefluxed
  8. temperatureby heating for 2 hours
  9. stirringunder stirring
  10. temperatureThen, the reaction solution was cooled to room temperature
  11. customto separate the solution into layers
  12. customThe organic layer separated
  13. washwas washed with water
  14. dry with materialan aqueous solution of saturated sodium hydrogencarbonate and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate
  15. customThe drying agent was separated by filtration
  16. concentrationthe filtrate was concentrated under reduced pressure
  17. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=30:1)

Sources & evidence

ORD record
ord-2df366128e7f487ab7cbc4649cd2ee85
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

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