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

HRID 386384

Reaktionsgleichung

Reaktionsgleichung von HRID 386384
[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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-900794aa6d0849628b825587973780c5
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372807B2

Verknüpfte Notizen

Wird geladen…