反応 #435478

反応方程式

Na2CO3

BF3 Et2O

triethylsilane

3-(4Benzyloxynaphthalen-1-yl)-2-phenoxy-3-hydroxy-2-methylpropionic acid ethyl ester

→

2-Phenoxy-3-(4-benzyloxynaphthalen-1-yl)-2-methylpropionic acid ethyl ester

溶媒

CH2Cl2

反応条件

後処理

1. 1
   workup.STIRRINGthe mixture was stirred vigorously for 15 min
2. 2
   その他The solution was partitioned
3. 3
   洗浄the organic layer was washed twice with water and brine
4. 4
   乾燥dried over Na2SO4
5. 5
   濃縮concentrated in vacuo to 3-(4-benzyloxynaphthalen-1-yl)-2-phenoxy-2-methylpropionic acid ethyl ester as a golden oil (1.55 g, 89%)

実験手順

3-(4Benzyloxynaphthalen-1-yl)-2-phenoxy-3-hydroxy-2-methylpropionic acid ethyl ester (1.80 g, 3.9 mmol) in anhydrous CH2Cl2 (20 mL) was cooled to 0° C. and treated with BF3-Et2O (0.48 mL, 3.9 mmol, d=1.154) and triethylsilane (0.63 mL, 3.9 mmol, d=0.728). The mixture was stirred for 2 hr, gradually warming to ambient temperature. Saturated aqueous Na2CO3 (15 mL) was added and the mixture was stirred vigorously for 15 min. The solution was partitioned and the organic layer was washed twice with water and brine, dried over Na2SO4, and concentrated in vacuo to 3-(4-benzyloxynaphthalen-1-yl)-2-phenoxy-2-methylpropionic acid ethyl ester as a golden oil (1.55 g, 89%). Rf=0.41 (9:1 hexanes:ethyl acetate). 1H NMR (300 MHz, CDCl3): δ 8.33 (d, 1H, J=8.3), 8.11 (d, 1H, J=8.3), 7.47 (d, 2H, J=7.8), 7.40 (t, 1H, J=8.3), 7.37 (t, 1H, J=8.3), 7.36 (t, 2H, J=7.8) 7.28 (d, 2H, J=7.8), 7.11 (t, 2H, J=8.8), 6.87 (t, 1H, J=7.8), 6.79 (d, 1H, J=7.8), 6.69 (d, 2H, J=8.8), 5.18 (s, 2H, 4.08 (q, 2H, J=7.0), 3.66 (d, 1H, J=14.4), 3.54 (d, 1H, J=14.4), 1.38 (s, 3H), 1.13 (t, 3H, J=7.0). MS [EI+] 458 (M+NH4)+

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