Ethyl diazoacetate → (2-Phenoxy)ethoxyacetic Acid Ethyl Ester

HRID 18820

Reaktionsgleichung

Reaktionsgleichung von HRID 18820
[O:1]([CH2:8][CH2:9][OH:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[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:10][CH2:9][CH2:8][O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH3:18]

Komponenten

6

Edukt 2

HCID 12192Ethyl diazoacetateHCID 31236Phenoxyethanol

Produkt 1

HCID 33787264(2-Phenoxy)ethoxyacetic Acid Ethyl EsterAusbeute 82,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a solution of 2-phenoxyethan-1-ol (1.5 mL, 12.7 mmol) in dichloromethane (50 mL) is added rhodium (II) acetate dimer (10 mg) followed by ethyl diazoacetate (1.1 mL, 10.5 mmol). The reaction mixture is stirred at rt overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled to give 1.95 g of the product 440. 1H NMR (CDCl3) δ 7.40-7.25 (m, 2 H), 7.10-6.90 (m, 3 H), 4.30-4.15 (m, 5 H), 4.15-4.05 (m, 1 H), 4.05-3.90 (s, 2 H), 1.28 (t, 3 H)

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationthe residue vacuum distilled

Quellen und Nachweise

ORD-Eintrag
ord-bddd5ba06d964adc9306de3088a92f1f
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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