Hydrochloric Acid → Ethyl 2-(naphthalen-1-yl)-3-oxobutanoate

HRID 386384

反応式

HRID 386384 の反応式
[C:1]1([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[C:27](OC(=O)C)(=[O:29])[CH3:28].Cl>O1CCCC1>[C:1]1([CH:11]([C:27](=[O:29])[CH3:28])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7918Acetic AnhydrideHCID 62428alpha-Naphthaleneacetic acid, ethyl esterHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 54265160Ethyl 2-(naphthalen-1-yl)-3-oxobutanoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of ethyl 2-(naphthalen-1-yl)acetate (1 g, 4.7 mmol) in tetrahydrofuran (20 mL) at −78° C. was added LiHMDS (1M THF, 9.4 mL, 9.4 mmol) and the reaction mixture stirred at −78° C. for 1 hour. Acetic anhydride was then added (0.54 mL, 5.64 mmol) dropwise and the reaction allowed to warm to room temperature and stirred for 30 minutes. Aqueous HCl solution (1N, 25 mL) was added to the reaction mixture and then extracted with ethyl acetate, dried over sodium sulfate and concentrated to give compound ethyl 2-(naphthalen-1-yl)-3-oxobutanoate as a light yellow oil, that was used in the next step without further purification.

後処理

  1. temperatureto warm to room temperature
  2. stirringstirred for 30 minutes
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-900794aa6d0849628b825587973780c5
出典データセット
uspto-grants-2013_02
特許番号
US08372807B2

関連ノート

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