反応 #326252

反応方程式

methanol

LiBH4

NH4Cl

229

3-(3-{2-[3-(2-Ethoxycarbonyl-2-methylpropyl}-phenyl]-[1,3]dithian-2-yl)-phenyl)-2,2-dimethylpropionic acid ethyl ester

→

230

収率 85.2%

3-(3-{2-[3-(3-Hydroxy-2,2-dimethylpropyl)-phenyl]-[1,3]dithian-2-yl}-phenyl)-2,2-dimethylpropan-1-ol

収率 85.2%

溶媒

CH2Cl2

CH2Cl2

反応条件

後処理

1. 1
   温度the reaction mixture was heated
2. 2
   温度to reflux for 6 h
3. 3
   その他the layers were separated
4. 4
   抽出The aqueous layer was extracted with CH2Cl2 (2×10 mL)
5. 5
   乾燥The combined organic layers were dried over anhydrous Na2SO4
6. 6
   濃縮concentrated in vacuo

実験手順

To a suspension of LiBH4 (0.78 g, 35.8 mmol) in CH2Cl2 (55 mL) was added methanol (1.04 g, 32.5 mmol) at room temperature. After the addition of 229 (6.5 g, 12.3 mmol), the reaction mixture was heated to reflux for 6 h. After cooling to room temperature, saturated aqueous NH4Cl solution (20 mL) and CH2Cl2 (15 mL) were added and the layers were separated. The aqueous layer was extracted with CH2Cl2 (2×10 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to afford 230 (4.66 g, 85%) as an oil. 1H NMR (CDCl3): δ 7.42 (s br., 2 H), 7.17 (m, 4 H), 6.97 (m, 2 H), 3.63 (s, 4 H), 3.16 (s, 4 H), 2.69 (m, 2 H), 2.47 (m, 4 H), 1.88 (m, 2 H), 0.75 (s, 12 H). 13C NMR (CDCl3): δ 142.39, 139.18, 131.69, 129.88, 128.05, 127.01, 71.12, 44.89, 43.74, 36.70, 29.63, 24.22.

出典