Hydrochloric Acid → Ethyl 3-propoxycinnamate

HRID 1169493노트

반응식

HRID 1169493 반응식
C(OP([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(OCC)=O)C.[H-].[Na+].[CH2:17]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=O)[CH2:18][CH3:19].Cl>C1COCC1.O>[CH2:17]([O:20][C:21]1[CH:22]=[C:23]([CH:26]=[CH:27][CH:28]=1)[CH:24]=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:18][CH3:19]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 27604693-Propoxybenzaldehyde

생성물 1

HCID 70025296Ethyl 3-propoxycinnamate수율 104.5%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To ethyl diethylphosphonoacetate (24.7 g) was added THF (200 ml), and sodium hydride (60%, 4.4 g) was added at 0° C. to the resulting mixture, to which was then added dropwise a solution of 3-propoxybenzaldehyde (16.1 g) in THF (100 ml). The resulting mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into water, was neutralized with hydrochloric acid and was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with anhydrous magnesium sulfate. After concentration under reduced pressure to remove the solvent, the residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1) to obtain ethyl 3-propoxycinnamate (24.0 g) as a yellow oil.

후처리

  1. additionwas added at 0° C. to the resulting mixture, to which
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with an aqueous saturated solution of sodium chloride
  4. dry with materialwas dried with anhydrous magnesium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customto remove the solvent
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=6:1)

출처 및 근거

ORD 기록
ord-e8c985785ff64e4894904a22fa2ca67c
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06627651B1

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