Reaktion #1185254

Reaktionsgleichung

Imidazole

TBDMSCl

2-hydroxy-hexanoic acid ethyl ester

Water

→

title product

Ausbeute 96.7%

ethyl 2-{[tert-butyl(dimethyl)silyl]oxy}hexanoate

Ausbeute 96.7%

Lösungsmittel

DMF

diethyl ether

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe two phases were separated
2. 2
   ExtraktionThe aqueous phase was extracted with diethyl ether
3. 3
   Waschenwashed sequentially with 0.5 M HCl and water
4. 4
   Trocknendried over MgSO4
5. 5
   Einengenconcentrated in vacuo

Vorschrift

Imidazole (4.10 g, 60.22 mmol) and TBDMSCl (3.60 g, 23.89 mmol) was added to a stirred solution of 2-hydroxy-hexanoic acid ethyl ester (3.20 g, 19.97 mmol) in DMF (25 mL). The reaction mixture was kept at ambient temperature for 18 hrs. Water and diethyl ether were added and the two phases were separated. The aqueous phase was extracted with diethyl ether. The organic extracts were combined and washed sequentially with 0.5 M HCl and water, dried over MgSO4 and concentrated in vacuo to give the title product (5.30 g), 1H NMR (300 MHz, CDCl3) δ 4.18 (m, 3H), 1.69 (m, 2H), 1.35 (m, 4H), 1.28 (t, 3H), 0.91 (m, 12H), 0.07 (d, 6H).

Quelle