Ethyl diazoacetate → Ethyl [(3-methoxyphenyl)methoxy]acetate

HRID 18806

Reaktionsgleichung

Reaktionsgleichung von HRID 18806
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][OH:7].[N+](=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][O:7][CH2:6][C:5]1[CH:8]=[CH:9][CH:10]=[C:3]([O:2][CH3:1])[CH:4]=1)[CH3:18]

Komponenten

6

Edukt 2

HCID 12192Ethyl diazoacetateHCID 814373-Methoxybenzyl alcohol

Produkt 1

HCID 28940145Ethyl [(3-methoxyphenyl)methoxy]acetateAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittelHCID 8900HeptaneLösungsmittel

Versuchsvorschrift

To a solution of 3-methoxybenzyl alcohol (1.24 g, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (0.95 mL, 9.0 mmol). The reaction mixture is stirred at RT for 30 min. The reaction mixture is diluted with heptane, filtered through Celite, and the filtrate is evaporated and the residue is vacuum distilled at 150° C. to give 2.00 g of the product 398. 1H NMR (CDCl3) δ 7.26 (t, 1H), 6.93 (m, 2H), 6.85 (m, 1H), 4.62 (s, 2H), 4.23 (q, 2H), 4.09 (s, 2H), 3.81 (s, 3H), 1.29 (t, 3H); MS: m/z 224 (M++1).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 150° C.

Quellen und Nachweise

ORD-Eintrag
ord-341b35e602af476d9d8ada35dc20b078
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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