Tetrahydrofurfuryl alcohol → (Tetrahydrofuran-2-ylmethoxy)acetic Ethyl Ester

HRID 18833

Reaktionsgleichung

Reaktionsgleichung von HRID 18833
[CH2:1]([OH:7])[CH:2]1[O:6][CH2:5][CH2:4][CH2:3]1.[N+](=[CH:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[N-]>ClCCl.CCCCCCC.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:14]([O:13][C:11](=[O:12])[CH2:10][O:7][CH2:1][CH:2]1[CH2:3][CH2:4][CH2:5][O:6]1)[CH3:15]

Komponenten

6

Edukt 2

HCID 7360Tetrahydrofurfuryl alcoholHCID 12192Ethyl diazoacetate

Produkt 1

HCID 43119675(Tetrahydrofuran-2-ylmethoxy)acetic Ethyl EsterAusbeute 60,2 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

To a solution of tetrahydrofurfuryl alcohol (1.02 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 130° C. to give 1.02 g of the product 477. 1H NMR (CDCl3) δ 4.11 (q, 2H), 4.10 (s, 2H), 3.93 (m, 1H), 3.72 (m, 1H), 3.61 (m, 1H), 3.44 (m, 2H), 1.95-1.75 (m, 3H), 1.61-1.53 (m, 1H), 1.20 (t, 3H).

Aufarbeitung

  1. filtrationfiltered through Celite
  2. customthe filtrate is evaporated
  3. distillationdistilled at 130° C.

Quellen und Nachweise

ORD-Eintrag
ord-204f5de948154c3eb146710bb643fd31
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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