تفاعل #411359

معادلة التفاعل

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

المردود 78.4%

المذيبات

H2O

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe mixture was refluxed for 1 hours at 97° C
2. 2
   استخلاصextracted with ethyl acetate
3. 3
   غسيلThe organic layer was washed with saturated aqueous solution of sodium chloride
4. 4
   تجفيفdried with magnesium sulfate anhydride
5. 5
   تركيزconcentrated
6. 6
   غسيلthe elution
7. 7
   workup.ADDITIONwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1)

الإجراء التجريبي

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%.

المصدر