Реакция #1702036

Уравнение реакции

7

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

NaOH

→

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

Растворители

THF

water

water

Условия реакции

Обработка

1. 1
   Другоеtransferred to a separatory funnel
2. 2
   Экстракцияextracted with ether
3. 3
   Экстракцияextracted with ether (2×15 mL)
4. 4
   СушкаThe combined organic layers were dried (Na2SO4)
5. 5
   Концентрированиеconcentrated in vacuo
6. 6
   Другоеto afford (3S)-1 (187 mg, 93%) as a colorless oil that
7. 7
   Другоеwas used without further purification

Методика

To a solution of 7 (187 mg, 0.729 mmol, 1.0 equiv) in THF (2.5 mL) was added a solution of NaOH (32.) mg, 0.802 mmol, 1.1 equiv) in water (1 L). The reaction mixture was stirred at rt for 2 h, transferred to a separatory funnel, diluted with water (5 mL) and extracted with ether. The aqueous layer was acidified with 2 N HCl (3 mL) and extracted with ether (2×15 mL). The combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford (3S)-1 (187 mg, 93%) as a colorless oil that was used without further purification: ATR/IR 2920, 2851, 1709, 1412, 1189, 1079, 738 cm−1; 1H NMR (CDCl3) 4.85-4.7 (m, 1H), 3.55-3.45 (m, 1H), 3.39, 3.38 (2s, 3H), 2.56-2.52 (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) 176.5, 175.8, 81.5, 78.7, 68.0, 65.3, 56.7, 55.9, 41.5, 39.6, 39.0, 32.8, 32.6, 31.8, 29.7, 29.5, 29.2, 25.1, 24.4, 22.6, 14.1; MS (EI) m/z 274 (M+, 0.5), 256 (0.5), 171, 25, 129 (100), 97 (15).

Источник