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

HRID 1610400

反応式

HRID 1610400 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-d4367cef70914e0fb9caebac28dcb0ac
出典データセット
uspto-grants-2006_01
特許番号
US06982348B2

関連ノート

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