Reaktion #990094

Reaktionsgleichung

compound

2-(3-Tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester 1-ethyl ester

NaOH

→

product

2-(3-Tritylsulfanyl-propyl)-succinic acid 4-tert-butyl ester

Lösungsmittel

methanol

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigemost of the methanol has evaporated
2. 2
   ExtraktionThe water phase was extracted two times with ether
3. 3
   ExtraktionThe water phase was extracted three times with ethyl acetate
4. 4
   TrocknenThe recombined organic phase was dried over sodium sulfate
5. 5
   Filtrationfiltered
6. 6
   Sonstigeevaporated

Vorschrift

To a solution of the compound of example 28 (3.00 g, 5.78 mmol) in methanol (30 mL) and water (10 mL) was added NaOH (1N, 11.6 mL, 11.6 mmol). The mixture was stirred vigorously under ambient conditions. After 24 hours, most of the methanol has evaporated. The residue was portioned between water and ether. The water phase was extracted two times with ether, then acidified with HCl (1N) to pH 1. The water phase was extracted three times with ethyl acetate. The recombined organic phase was dried over sodium sulfate, filtered, and evaporated. The residue was flashed using 5% methanol in chloroform to give the product as a white solid. 1H-NMR(CDCl3, 400 MHz: 1.45(s, 9H); 1.35-1.64(m, 4H); 1.58(m, 1H); 2.16(m, 2H); 2.26(m, 1H); 2.64(m, 1H); 4.12(q, J=7.1 Hz, 2H), 7.19-7.29, 7.40(m, 15H).

Quelle