Potassium Carbonate → HCID 54552494, compound

HRID 1603942Notes

Reaction equation

HRID 1603942 reaction equation
[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:20][CH2:21][CH:22](P(OCC)(OCC)=O)[C:23]([O:25][CH2:26][CH3:27])=[O:24].C(=O)([O-])[O-].[K+].[K+]>>[CH3:1][O:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[C:22]([CH2:21][CH3:20])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:5][C:4]=1[O:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 3

HCID 11430Potassium CarbonateHCID 229053Ethyl 2-(diethoxyphosphoryl)butanoateHCID 217163814-Methoxy-3-(2-phenylethoxy)benzaldehyde

Product 1

HCID 54552494HCID 54552494, compoundYield 58%

Procedure

A mixture of 4-methoxy-3-(2-phenylethoxy)benzaldehyde (5.09 g), triethyl 2-phosphonobutyrate (10.76 g) and an aqueous solution of 6 M potassium carbonate (8.3 ml) was heated to 150° C. (oil bath temperature) and stirred vigorously for 8 hours. After the reaction mixture was cooled to room temperature, it was extracted with toluene. The toluene extract was washed with an aqueous solution of 0.5 N sodium hydroxide and a saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate. The drying agent was separated by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=25:1) to obtain 4.08 g of ethyl 3-[4-methoxy-3-(2-phenylethoxy)phenyl]-2-ethylacrylate as a mixture of E- and Z-isomers (E-isomer:Z-isomer=5. 7:1).

Workup

  1. extractionit was extracted with toluene
  2. extractionThe toluene extract
  3. washwas washed with an aqueous solution of 0.5 N sodium hydroxide
  4. dry with materiala saturated aqueous solution of NaCl in consecutive order and dried over anhydrous magnesium sulfate
  5. customThe drying agent was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=25:1)

Sources & evidence

ORD record
ord-4ca0851a478a4afe85d425af084efce0
Source dataset
uspto-grants-1999_11
Patent number
US05990151

Reaction notes

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