Reaktion #2162964

Reaktionsgleichung

lithium aluminum hydride

2,2′-diselenobis(5-fluorobenzoic acid)

2,2′-diselenobis(5fluorobenzoic acid)

→

2,2′-diselenobis(5-fluorobenzyl alcohol)

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   TemperaturAfter refluxing for 50 minutes
3. 3
   Sonstigethe mixture was quenched with 20 mL of water
4. 4
   Extraktionextracted with ethyl acetate
5. 5
   workup.WAITThe aqueous solution was left
6. 6
   Sonstigesitting overnight with consequent precipitation of 815 mg (42%) of 137 as yellow needles with mp 112° C

Vorschrift

To lithium aluminum hydride (0.89 g, 23 mmol) in dry tetrahydrofuran (20 mL) under argon at room temperature, 2,2′-diselenobis(5-fluorobenzoic acid) (116) (2.05 g, 4.70 mmol) dissolved in 10 mL of dry tetrahydrofuran was added dropwise. After refluxing for 50 minutes, the mixture was quenched with 20 mL of water and extracted with ethyl acetate. The aqueous solution was left sitting overnight with consequent precipitation of 815 mg (42%) of 137 as yellow needles with mp 112° C. IR (KBr) 3214 (broad), 1577, 1016, 874, 814 cm−1; 1H NMR (300 MHz) δ 7.52 (dd, J=8.2 Hz, 5.6 Hz, 1H), 7.24 (dd, J=9.8 Hz, 1H), 6.89 (dt, J=8.2 Hz, 3.1 Hz, 1 H), 4.69 (s, 2H), 2.06 (br s, 1H); mass spectrum, m/z (relative intensity) 410 (10, M+), 188 (23), 123 (16), 96 (100), 75 (16). Exact mass calcd for C14H12O2F280Se: 409.9134. Found: 409.9132.

Quelle