Réaction #1702035

Équation de réaction

6

(4R)-4-((2RS)-2-Methoxyundecyl)oxetan-2-one

NaOH

→

(3R,5RS)-3-Hydroxy-5-methoxytetradecanoic acid

Solvants

THF

water

Conditions de réaction

Traitement

1. 1
   Autrechanged from turbid to clear (t=about 0.5 h)
2. 2
   AutreThe solution was quenched by addition of 1 M HCl (1 mL)
3. 3
   Extractionextracted with ether (2×5 mL)
4. 4
   LavageThe combined organic layers were washed with water (5 mL) and brine (5 mL)
5. 5
   Séchagedried (Na2SO4)
6. 6
   Concentrationconcentrated in vacuo
7. 7
   Autreto afford a pale yellow oil
8. 8
   AutrePurification of the crude product by chromatography on SiO2 (1:1 EtOAc/hexanes containing 0.5% AcOH)
9. 9
   Autreprovided (3R)-1 (94.4 mg, 96%) as a colorless oil

Mode opératoire

(ref. Gu, et al. Nature 459, 731-735 (2009)). To a solution of 6 (92.0 mg, 0.359 mmol, 1.0 equiv) in THF (1.5 mL) was added a solution of NaOH (15.7 mg, 0.394 mmol, 1.1 equiv) in water (1.5 mL). The reaction mixture was stirred at rt for 1 h. During this time, its appearance changed from turbid to clear (t=about 0.5 h). The solution was quenched by addition of 1 M HCl (1 mL) and extracted with ether (2×5 mL). The combined organic layers were washed with water (5 mL) and brine (5 mL), dried (Na2SO4) and concentrated in vacuo to afford a pale yellow oil. Purification of the crude product by chromatography on SiO2 (1:1 EtOAc/hexanes containing 0.5% AcOH) provided (3R)-1 (94.4 mg, 96%) as a colorless oil: ATR/IR 2920, 2851, 1709, 1413, 1187, 1079, 736 cm−1; 1H NMR (CDCl3) 4.35-4.20 (m, 1H), 3.55-3.45 (m, 1H), 3.38, 3.37 (2s, 3H), 2.56-2.50 (m, 2H), 1.80-1.35 (m, 3H), 1.35-1.25 (m, 14H), 0.90 (t, 3H, J=6.9 Hz); 13C NMR (CDCl3) 176.4, 175.7, 68.1, 65.4, 56.7, 56.0, 41.6, 41.5, 39.7, 39.1, 32.9, 32.8, 31.9, 29.8, 29.6, 29.5, 29.3, 25.2, 24.5, 22.7, 14.1.

Source