反応 #1857549

反応方程式

(S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhex-4-enoate

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title compound

収率 98.4%

(S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhexanoate

収率 98.4%

溶媒

MeOH

反応条件

後処理

1. 1
   ろ過The mixture was filtered through a plug of Celite®
2. 2
   洗浄the plug was washed with MeOH (20 mL)
3. 3
   その他the solvent was removed under reduced pressure
4. 4
   workup.DISSOLUTIONthe residue was dissolved in DCM (50 mL)
5. 5
   その他to remove residual water (H2O)
6. 6
   その他the solvent was removed under reduced pressure

実験手順

To a well stirred solution of (S)-methyl 2-((S)-1-hydroxyethyl)-5-methylhex-4-enoate (9.5 g, 51.0 mmol) in MeOH (51 mL) was added 10% Pd/C (0.543 g, 5.10 mmol). The reaction was put under a hydrogen atmosphere (balloon) and stirred at room temperature for 20 h. The mixture was filtered through a plug of Celite® and the plug was washed with MeOH (20 mL). The filtrate and washes were combined, the solvent was removed under reduced pressure, and the residue was dissolved in DCM (50 mL). The solution was passed through a phase separator to remove residual water (H2O), and the solvent was removed under reduced pressure to afford the title compound (9.45 g, 50.2 mmol, 98%) as a slightly yellow oil: IR (thin film) 3451, 2954, 2871, 1736, 1719, 1169 cm−1; 1H NMR (400 MHz, CDCl3) δ 3.91 (p, J=6.4 Hz, 1H), 3.72 (s, 3H), 2.77 (s, 1H), 2.36 (ddd, J=9.2, 6.3, 5.0 Hz, 1H), 1.72-1.45 (m, 3H), 1.28-1.05 (m, 5H), 0.88 (dd, J=6.6, 3.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 176.13, 68.55, 53.29, 51.67, 36.55, 28.16, 27.37, 22.74, 22.44, 21.68.

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