反応 #66045

反応方程式

51

Methyl (2R)-2-acetamido-3-(4-hydroxyphenyl)propanoate

K2CO3

allyl bromide

→

title compound

収率 85.4%

Methyl (2R)-2-acetamido-3-(4-allyloxyphenyl)propanoate

収率 85.4%

溶媒

DMF

反応条件

後処理

1. 1
   その他The reaction was quenched with water (30 mL)
2. 2
   抽出extracted with ethyl acetate (3×30 mL)
3. 3
   洗浄the combined organics were washed with water (5×20 mL)
4. 4
   その他before drying
5. 5
   その他The solvent was evaporated

実験手順

To a solution of 51 (989 mg, 4.17 mmol), and anhydrous K2CO3 (1.15 g, 8.34 mmol) in DMF (10 mL) was added allyl bromide (1.01 g, 8.34 mmol) and the resulting mixture was allowed to stir for 16 h under a nitrogen atmosphere. The reaction was quenched with water (30 mL), extracted with ethyl acetate (3×30 mL), and the combined organics were washed with water (5×20 mL) before drying. The solvent was evaporated to yield the title compound (985 mg, 3.56 mmol, 85%) as a pale yellow solid. [α]D25-24.2 (c. 0.1, EtOH). Mp 90° C. 1H NMR (CDCl3, 300 MHz): δ 6.97 (d, J=8.7 Hz, 2H, ArH2′ and ArH6′); 6.80 (d, J=8.7 Hz, 2H, ArH3′ and ArH5′); 6.09 (d, J=7.8 Hz, 1H, NH); 6.01 (m, 1H, H2″); 5.37 (dd, J=1.8, 17.4 Hz, 1H, H3a″); 5.25 (dd, J=1.8, 10.5 Hz, 1H, H3b″); 4.80 (m, 1H, H2); 4.47 (d, J=5.5 Hz, 2H, H1″); 3.68 (s, 3H, OCH3); 3.04 (m, 2H, H3); 1.99 (s, 311, NCOCH3). Mass Spectrum (CI, +ve) m/z 278 (100%) [MH+]. HRMS (EI) calcd for C15H19NO4 277.131408, found 277.130309.

出典