反応 #1869210

反応方程式

2-Methoxybenzylamine

acetic anhydride

→

subtitled compound

収率 40.4%

N-(2-Hydroxybenzyl)acetamide

収率 40.4%

溶媒

methanol

反応条件

後処理

1. 1
   その他The volatiles were removed in vacuo
2. 2
   workup.DISSOLUTIONThe residue was dissolved in CH2Cl2
3. 3
   workup.ADDITION1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly
4. 4
   workup.ADDITIONAfter addition
5. 5
   温度cooled to 0° C.
6. 6
   workup.ADDITIONmethanol (3 mL) was added and after 10 min volatiles
7. 7
   その他were removed in vacuo
8. 8
   workup.DISSOLUTIONThe residue was dissolved in ethyl acetate
9. 9
   洗浄washed successively with aqueous NaHCO3 and H2O
10. 10
    乾燥The organic layer was dried over Na2SO4
11. 11
    ろ過filtered
12. 12
    濃縮concentrated
13. 13
    その他The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum spirit)

実験手順

2-Methoxybenzylamine (822 mg, 6.0 mmol) in methanol (10 mL) was treated with acetic anhydride (613 mg, 6.0 mmol) at room temperature for 2 h. The volatiles were removed in vacuo. The residue was dissolved in CH2Cl2, cooled to 0° C., 1M solution of BBr3 in CH2Cl2 (12 mL, 12.0 mml) was added slowly. After addition was completed the reaction mixture was stirred at room temperature overnight, cooled to 0° C., methanol (3 mL) was added and after 10 min volatiles were removed in vacuo. The residue was dissolved in ethyl acetate, washed successively with aqueous NaHCO3 and H2O. The organic layer was dried over Na2SO4 filtered and concentrated. The residue was purified by silica gel flash chromatography (0-50% ethyl acetate in petroleum spirit) to give the subtitled compound (400 mg).

出典