Methyl iodide → Ethyl 2-(4-methylphenyl)propanoate

HRID 239073

Reaktionsgleichung

Reaktionsgleichung von HRID 239073
[CH2:1]([O:3][C:4](=[O:13])[CH:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:6])[CH3:2].[C:14]1(C)C=CC(CC(OCC)=O)=CC=1.[Li+].CC([N-]C(C)C)C.CI>C1COCC1.CN1C(=O)N(C)CCC1>[C:10]1([CH3:14])[CH:11]=[CH:12][C:7]([CH:5]([CH3:6])[C:4]([O:3][CH2:1][CH3:2])=[O:13])=[CH:8][CH:9]=1

Komponenten

7

Edukt 4

HCID 6328Methyl iodideHCID 84175Ethyl p-tolylacetateHCID 99643Benzeneacetic acid, alpha-methyl-, ethyl esterHCID 2724682Lithium diisopropylamide

Produkt 1

HCID 11070524Ethyl 2-(4-methylphenyl)propanoateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Lösungsmittel

Versuchsvorschrift

According to the procedure given for the synthesis of 202, ethyl p-tolylacetate (2.72 g, 15.2 mmol) was reacted with LDA (7.6 mL, 15.25 mmol) and methyl iodide (3.03 g, 21.30 mmol) in anhydrous THF (70 mL) and DMPU (1 mL). After aqueous workup and extraction, the residue was distilled in high vacuo to give 203 (2.5 g, 86.0%) as an oil. Bp 59-63° C./0.2 mmHg. 1H NMR (CDCl3): δ (ppm) 7.18 (d, 2 H, J=8.1), 7.10 (d, 2 H, J=8.1), 4.09 (m, 2 H), 3.67 (q, 1 H, J=7.2), 2.29 (s, 3 H), 1.47 (d, J=7.2 Hz, 3 H), 1.20 (t, J=5.7 Hz, 3 H). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 174.71, 137.80, 136.63, 129.33, 129.14, 127.36, 60.66, 45.18, 21.05, 18.70, 14.15.

Aufarbeitung

  1. extractionAfter aqueous workup and extraction
  2. distillationthe residue was distilled in high vacuo

Quellen und Nachweise

ORD-Eintrag
ord-af776805c1c24e9e8a397dbeb88e47ea
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642653B2

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