Cyclopentanol → Ethyl 2-(cyclopentyloxy)acetate

HRID 18821

Reaktionsgleichung

Reaktionsgleichung von HRID 18821
[CH:1]1([OH:6])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N+](=[CH:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:13]([O:12][C:10](=[O:11])[CH2:9][O:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:14]

Komponenten

6

Edukt 2

HCID 7298CyclopentanolHCID 12192Ethyl diazoacetate

Produkt 1

HCID 43119653Ethyl 2-(cyclopentyloxy)acetateAusbeute 67,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a solution of cyclopentanol (0.91 mL, 9.5 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 overnight. The reaction mixture is diluted with heptane, and filtered. The filtrate is evaporated, and the residue vacuum distilled at 150° C. to give 1.04 g of the product 444. 1H NMR (CDCl3) δ 4.21 (q, 2 H), 4.04 (s, 2 H), 1.85-1.45 (m, 8 H), 1.29 (t, 3 H)

Aufarbeitung

  1. filtrationfiltered
  2. customThe filtrate is evaporated
  3. distillationthe residue vacuum distilled at 150° C.

Quellen und Nachweise

ORD-Eintrag
ord-42c89541970c460c82e2aa4dc5db327e
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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