Diethyl Malonate → Ethyl 2,9-diethoxycarbonylnonanoate

HRID 2268440노트

반응식

HRID 2268440 반응식
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].[Cl-].[NH4+]>C(O)C>[CH2:10]([O:9][C:1]([CH:2]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[O:8])[CH3:11]

참가 물질

6

반응물 4

HCID 7761Diethyl MalonateHCID 25517Ammonium ChlorideHCID 264813Ethyl 8-bromooctanoateHCID 2723922Sodium ethoxide

생성물 1

HCID 18348648Ethyl 2,9-diethoxycarbonylnonanoate수율 67.4%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

Diethyl malonate (9.85 g, 61.5 mmols) was added to an ethanol (170 ml) solution of sodium ethoxide (4.61 g, 67.7 mmols) with cooling with ice, and then stirred for 15 minutes at room temperature, and thereafter ethyl 8-bromooctanoate (17.0 g, 67.7 mmols) was added thereto. The reaction mixture was heated under reflux for 2 hours, and then an aqueous saturated ammonium chloride solution was added thereto, and extracted with ethyl acetate. The organic layer was washed with water and a saturated aqueous sodium chloride solution, then dried, and concentrated in vacuo. The thus-obtained crude product was purified by silica gel column chromatography (hexane:ethyl acetate=20:1) to obtain the entitled compound (13.7 g) as an oil.

후처리

  1. temperaturewith cooling with ice
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 2 hours
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, then dried
  7. concentrationconcentrated in vacuo
  8. customThe thus-obtained crude product
  9. customwas purified by silica gel column chromatography (hexane:ethyl acetate=20:1)

출처 및 근거

ORD 기록
ord-33d2b3341d964e5e945fa83036a9038e
출처 데이터셋
uspto-grants-2001_12
특허 번호
US06326369B1

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