Methanol → (Tetrahydropyran-2-yl)methoxyacetic Acid Ethyl Ester

HRID 18826

Reaktionsgleichung

Reaktionsgleichung von HRID 18826
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[CH2:7][OH:8].[N+](=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[N-].CO>ClCCl.CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.[Rh].[Rh]>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][O:8][CH2:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)[CH3:16]

Komponenten

6

Edukt 3

HCID 887MethanolHCID 7524Tetrahydropyran-2-methanolHCID 12192Ethyl diazoacetate

Produkt 1

HCID 43119671(Tetrahydropyran-2-yl)methoxyacetic Acid Ethyl EsterAusbeute 82,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

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

Versuchsvorschrift

To a solution of tetrahydropyran-2-methanol (1.13 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 (0.5 mL), and the solvents rotary evaporated. The residue is purified by chromatography on silica gel; elution with EtOAc:heptane (30:70) gives 1.66 g of the product 458. 1H NMR (CDCl3) δ 4.3-4.1 (m, 4 H), 4.0 (m, 1 H), 3.6-3.4 (m, 4 H), 1.85 (m, 1 H), 1.6-1.3 (m, 5 H), 1.25 (t, 3 H); MS: m/z 203 (M++1).

Aufarbeitung

  1. customThe residue is purified by chromatography on silica gel
  2. washelution with EtOAc:heptane (30:70)

Quellen und Nachweise

ORD-Eintrag
ord-0df910265dde4c77bbc68820210fb1a0
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07741493B2

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