反応 #460367

反応方程式

ammonium chloride

n-butyllithium

3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal

product

3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal

methyl acetate

diisopropylamine

→

product

methyl 5-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-3-hydroxypentanoate

溶媒

hexane

THF

THF

tetrahydrofuran

反応条件

後処理

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction mixture was stirred at -78° C. for 1/2 hr
3. 3
   温度to warm to room temperature
4. 4
   抽出The mixture was extracted with ether
5. 5
   抽出The ether extract
6. 6
   洗浄was washed with water
7. 7
   乾燥dried over anydrous MgSO4
8. 8
   workup.DISTILLATIONdistilled to dryness under reduced pressure
9. 9
   その他The residual oil was chromatographed on silica gel
10. 10
    洗浄Elution with hexane-ethyl acetate
11. 11
    その他followed by crystallization from aqueous methanol

実験手順

To a solution of 1.5 g of diisopropylamine in 25 ml of tetrahydrofuran (THF), stirred at -78° C. in an atmosphere of nitrogen, was added 6.5 ml of 1.6M n-butyllithium in hexane. The mixture was stirred at -78° C. for 5 min after which a solution of 1.2 g of methyl acetate in 5 ml of THF was added. The mixture was again stirred at -78° C. for 5 min. Then a solution of 1.75 g of 3-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]propanal, the product of Example 3, in 20 ml of THF was added. The reaction mixture was stirred at -78° C. for 1/2 hr. A saturated solution of ammonium chloride was carefully added, and the resultant mixture was allowed to warm to room temperature. The mixture was extracted with ether. The ether extract was washed with water, dried over anydrous MgSO4, and distilled to dryness under reduced pressure. The residual oil was chromatographed on silica gel. Elution with hexane-ethyl acetate followed by crystallization from aqueous methanol gave the product mp. 77°-80° C.

出典