Methanol → 2-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl Ester

HRID 18819

Reaktionsgleichung

Reaktionsgleichung von HRID 18819
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[O:4][CH2:5][CH2:6][OH:7].[N+](=[CH:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N-].CO>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:18]([O:17][C:15](=[O:16])[CH2:14][O:7][CH2:6][CH2:5][O:4][C:3]1[CH:8]=[CH:9][CH:10]=[CH:11][C:2]=1[Cl:1])[CH3:19]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 12192Ethyl diazoacetateHCID 849332-(2-Chlorophenoxy)ethanol

Produkt 1

HCID 685707682-[2-(2-Chlorophenoxy)ethoxy]acetic Acid Ethyl EsterAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 423677Acetic acid, rhodium salt (4:2)KatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 2-(2-chlorophenoxy)ethanol (1.73 mL, 10.0 mmol) in dichloromethane (20 mL) is added rhodium (II) acetate dimer (11 mg) followed by ethyl diazoacetate (1.05 mL, 10.0 mmol). The reaction mixture is stirred at rt for 20 min. To the reaction mixture is added MeOH followed by rotary evaporated, and the residue is purified by chromatography on silica gel; elution with EtOAc:heptane (25:75) gives 1.36 g of the product 436. 1H NMR (CDCl3) δ 7.35 (d, 1 H), 7.19 (d, 1 H), 6.95-6.90 (m, 2 H), 4.30 (s, 2 H), 4.25-4.15 (m, 4 H), 4.0 (t, 2 H), 1.2 (t, 3 H); MS: m/z 259 (M++1).

Aufarbeitung

  1. customthe residue is purified by chromatography on silica gel
  2. washelution with EtOAc:heptane (25:75)

Quellen und Nachweise

ORD-Eintrag
ord-45a00ca672ec405ca7852abcbc0f4552
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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