تفاعل #94683

معادلة التفاعل

vinyl magnesium chloride

4-oxo-1-iodo-trans-1-octene

→

4-Hydroxy-4-vinyl-1-iodo-trans-1-octene

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter the addition
2. 2
   أخرىThe reaction is quenched with a mixture of hexane and ice
3. 3
   أخرىThe aqueous phase is separated
4. 4
   استخلاصextracted with additional hexane
5. 5
   غسيلThe combined hexane extracts are washed successively with water and brine
6. 6
   تجفيفThe solution is dried over magnesium sulfate
7. 7
   تركيزconcentrated
8. 8
   تجفيفto dry column chromatography on silica gel with benzene
9. 9
   أخرىto give a liquid, pmr spectrum (CDCl3)

الإجراء التجريبي

To a stirred solution of 7.8 ml of vinyl magnesium chloride (2.3M in tetrahydrofuran), at -25° C is added a solution of 3.55 g of 4-oxo-1-iodo-trans-1-octene in 20 ml of tetrahydrofuran during 15 minutes. After the addition, the solution is stirred at -20° C to -15° C for 30 minutes. The reaction is quenched with a mixture of hexane and ice. The aqueous phase is separated and extracted with additional hexane. The combined hexane extracts are washed successively with water and brine. The solution is dried over magnesium sulfate and concentrated. The residue is subjected to dry column chromatography on silica gel with benzene as developing solvent to give a liquid, pmr spectrum (CDCl3): 5.2 (m, terminal CH2), 5.83 (q, CH=CH2), 6.13 (d, ICH=), and 6.52 (m, ICM=CH).

المصدر