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

HRID 386384

Reaction equation

HRID 386384 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-900794aa6d0849628b825587973780c5
Source dataset
uspto-grants-2013_02
Patent number
US08372807B2

Linked notes

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