Ethyl chloroformate → Diethyl 2-(4-(benzyloxy)phenyl)malonate

HRID 2268454

Reaktionsgleichung

Reaktionsgleichung von HRID 2268454
[Li+].CC([N-]C(C)C)C.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:29](Cl)(=[O:33])[O:30][CH2:31][CH3:32].[Cl-].[NH4+]>C1COCC1.CCCCCCC>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][C:20]([CH:23]([C:29]([O:30][CH2:31][CH3:32])=[O:33])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:19][CH:18]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Komponenten

7

Edukt 4

HCID 10928Ethyl chloroformateHCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 27374284-Benzyloxyphenylacetic acid ethyl ester

Produkt 1

HCID 2823246Diethyl 2-(4-(benzyloxy)phenyl)malonateAusbeute 83,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

A heptane solution of LDA (2.0 M, 36.4 ml, 72.8 mmols) was dropwise added to a THF (130 ml) solution of ethyl 4-benzyloxyphenylacetate (13.1 g, 48.5 mmols) and ethyl chlorocarbonate (9.25 ml, 97.0 mmols), under a nitrogen stream at −70° C. or lower. The reaction mixture was stirred for 15 minutes, then a saturated aqueous ammonium chloride solution was added thereto, and the resulting mixture was allowed to warm to room temperature, and then extracted with diethyl ether. The organic layer was washed with a saturated aqueous sodium chloride solution, and then dried. The solvent was evaporated out in vacuo, and the resulting residue was washed with hexane to obtain the entitled compound (13.8 g) as crystals, which were further recrystallized from hexane.

Aufarbeitung

  1. extractionextracted with diethyl ether
  2. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  3. customdried
  4. customThe solvent was evaporated out in vacuo
  5. washthe resulting residue was washed with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a66fbab7e4fc423199e0d459f2cedd78
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06326369B1

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