Hydrochloric Acid → Ethyl 3-(naphthalen-8-yl)-3-oxopropanoate

HRID 1610400

반응식

HRID 1610400 반응식
[C:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:3])[CH3:2].C(O)C.[H-].[Na+].Cl.[C:20](=O)([O:24]CC)[O:21][CH2:22][CH3:23]>O>[C:4]1([C:1]([CH2:2][C:20]([O:21][CH2:22][CH3:23])=[O:24])=[O:3])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 7766Diethyl CarbonateHCID 136631-AcetylnaphthaleneHCID 24758Sodium hydride

생성물 1

HCID 2760157Ethyl 3-(naphthalen-8-yl)-3-oxopropanoate수율 95%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

To a solution of 1′-acetonaphthone (28.29 g, 0.1662 mmol) and ethanol (0.5 ml) in diethyl carbonate (200 ml) was added sodium hydride (13.3 g, 60% in oil, 0.332 mol) by small portions and the mixture was stirred at 80° C. for 1.5 hrs. The reaction solution was poured into water, acidified with dilute hydrochloric acid and extracted twice with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-6:1) to give ethyl (1-naphthoyl)acetate (38.14 g, 95%) as a yellow liquid.

후처리

  1. extractionextracted twice with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=20:1-6:1)

출처 및 근거

ORD 기록
ord-d4367cef70914e0fb9caebac28dcb0ac
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982348B2

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