Reaktion #984007

Reaktionsgleichung

compound ( 2d )

(5S)-5-(Pivaloyloxymethyl)-5H-furan-2-one

benzophenone

ethyl acetate

CHCl3

→

compound ( 3d )

Ausbeute 93.0%

(4S,5S)-5-(Pivaloyloxymethyl)-4-[1,3]dioxolan-2-yldihydrofuran-2-one

Ausbeute 93.0%

Lösungsmittel

[1,3]-dioxolane

—

hexanes

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas irradiated at 0° C. for 1.5 hours

Vorschrift

A solution containing 29.0 mg (0.146 mmol) compound (2d) and 3.0 mg (0.016 mmol) benzophenone in 20 mL [1,3]-dioxolane was irradiated at 0° C. for 1.5 hours according to the general procedure. Column chromatography (silica gel 15 g, ethyl acetate in hexanes 40%) gave compound (3d) (37 mg. 93%) as a colorless solid, Rf=0.21, [α]25D 23.8°, c 1.0, CHCl3, IR (neat) 1785, 1740, 1210, 740 cm−1; 1H-NMR (400 MHz, CDCl3) δ: 1.21 (s, 9H), 2.57-2.60 (m, 1H), 2.67-2.75 (m, 2H), 3.91-3.93 (m, 2H), 4.01-4.04 (m, 2H), 4.37 (dd, 1H, J=4.2 Hz, J=12.2 Hz), 4.38 (dd, 1H, J=2.9 Hz, J=12.2 Hz), 4.69 (mc, 1H), 4.92 (d, 1H, J=3.6 Hz). 13C-NMR (100.6 MHz, CDCl3, Dept) δ: 27.14 (+), 29.75 (−), 38.70 (+) (quat), 65.26 (−), 65.43 (−), 65.58 (−), 77.37 (+), 103.30 (+), 175.47 (quat), 178.02 (quat). C13H20O6; Exact Mass: 272.13; Mol. Wt.: 272.29; C, 57.34, H, 7.40, O, 35.25.

Quelle