反応 #411359

反応方程式

trimethyl orthobenzoate

5-(4-amino-3-hydroxy-5-methoxyphenyl)-4-t-butyl-3,3-dimethyl-2,3-dihydrofuran

Compound [ 61 ]

5-(4-amino-3-hydroxy-5-methoxyphenyl)-4-t-butyl-3,3-dimethyl-2,3-dihydrofuran

ethyl acetate

sodium hydrogencarbonate

→

4-t-butyl-5-(4-methoxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran

収率 78.4%

溶媒

H2O

反応条件

後処理

1. 1
   温度the mixture was refluxed for 1 hours at 97° C
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The organic layer was washed with saturated aqueous solution of sodium chloride
4. 4
   乾燥dried with magnesium sulfate anhydride
5. 5
   濃縮concentrated
6. 6
   洗浄the elution
7. 7
   workup.ADDITIONwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1)

実験手順

To 1.00 mL (5.82 mmol) of trimethyl orthobenzoate was added 204 mg (0.70 mmol) of 5-(4-amino-3-hydroxy-5-methoxyphenyl)-4-t-butyl-3,3-dimethyl-2,3-dihydrofuran (Compound [61]), and the mixture was refluxed for 1.5 hours at 150° C. To this reaction mixture, 2.0 ml of ethyl acetate, and 0.2 ml of H2O, and 10.1 mg (0.05 mmol) of TsOH H2O was added and the mixture was refluxed for 1 hours at 97° C. The resulting mixture was poured in saturated aqueous solution of sodium hydrogencarbonate and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried with magnesium sulfate anhydride, and concentrated. The residue was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1) to obtain 207 mg of 4-t-butyl-5-(4-methoxy-2-phenylbenzo[d]oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [62]). Yield 78.4%.

出典