Reaktion #47104

Reaktionsgleichung

tetrahydropyran-2-methanol

ethyl diazoacetate

MeOH

→

product 458

Ausbeute 82.1%

(Tetrahydropyran-2-yl)methoxyacetic acid ethyl ester

Ausbeute 82.1%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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).

Quelle