تفاعل #67887
ord-07fccfd5bd4c4dcc93af0ec0e0dd9b1c
معادلة التفاعل
المتفاعلات
الكواشف
ظروف التفاعل
المعالجة
- 1درجة الحرارةA 25 ml two-necked flask was flame
- 2أخرىdried
- 3درجة الحرارةto be cooled
- 4workup.ADDITIONadded to the reaction flask
- 5أخرىThe reaction was quenched with 40 ml saturated ammonium chloride (aq)
- 6workup.ADDITIONcontaining 0.4 ml ammonium hydroxide
- 7أخرىseparated
- 8استخلاصthe aqueous layer was extracted with ethyl acetate
- 9تجفيفdried over anhydrous magnesium sulfate
- 10ترشيحThe solid was filtered off
- 11أخرىThe solvent was evaporated off under vacuum
- 12أخرىThe crude product was purified by chromatography on silica gel using
- 13workup.ADDITIONa mixture of hexane and ethyl acetate as a gradient eluent
الإجراء التجريبي
A 25 ml two-necked flask was flame dried and allowed to be cooled. (S)-tert-butyl(1-iodooctan-3-yloxy)dimethylsilane (1.18 g, 3.2 mmol) and 11.8 L ether were added to the reaction flask, followed by dropwise addition of tert-butyl-lithium (3.75 ml, 1.7M in pentane) at −70° C. A homogenous solution of copper cyanide (0.29 g, 3.2 mmol) and methyllithium (1.6 ml, 2M in ether) in 5.8 ml ether was cooled from room temperature to −70° C. and added to the reaction flask while stirring for 30 minutes. Then, a solution of (R)-2-(3-(benzyloxy)benzyl)-4-(tert-butyldimethylsilyloxy)cyclopent-2-enone (0.65 g, 1.6 mmol) in 6.5 ml ether at −70° C. was added to the reaction mixture for 30 minutes. The reaction was quenched with 40 ml saturated ammonium chloride (aq) containing 0.4 ml ammonium hydroxide. The reaction mixture was phase separated and the aqueous layer was extracted with ethyl acetate. The organic layers were combined and dried over anhydrous magnesium sulfate. The solid was filtered off. The solvent was evaporated off under vacuum. The crude product was purified by chromatography on silica gel using a mixture of hexane and ethyl acetate as a gradient eluent. Yield of the titled compound was 1.1 g (85%).