تفاعل #1985946
ord-94763bb1c83c48a3b83869585f59d137
معادلة التفاعل
methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate
THF
triphenylphosphine
carbon tetrabromide
→
desired product
Methyl 5-Acetoxy-2-bromomethyl-4-methoxyhydrocinnamate
المتفاعلات
الكواشف
لا شيء
ظروف التفاعل
الظروف التفصيلية
See reaction.notes.procedure_details.
المعالجة
- 1ترشيحfiltered
- 2تركيزThe filtrate is concentrated in vacuo
- 3ترشيحthe residue purified by filtration through silica gel in 50% ethyl acetate in hexanes
- 4غسيلeluting with 25% ethyl acetate in hexanes
الإجراء التجريبي
To a solution of methyl 5-hydroxy-2-tert-butyldimethylsilyloxymethyl-4-methoxyhydrocinnamate (5.21 g) in carbon tetrabromide (12.35 g) in anhydrous ether (75 ml) and anhydrous THF (50 ml) is added portionwise triphenylphosphine (9.78 g) and the mixture stirred at room temperature for 60 minutes, diluted with ether, then filtered. The filtrate is concentrated in vacuo and the residue purified by filtration through silica gel in 50% ethyl acetate in hexanes followed by HPLC, eluting with 25% ethyl acetate in hexanes, to give the desired product.