反応 #81619

反応方程式

oxone

4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol

dimethylsulfoxide

oxalyl chloride

→

4-[4-[4-(hydoxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetaldehyde

溶媒

water

triethylamine

methylene chloride

methylene chloride

methylene chloride

methylene chloride

反応条件

後処理

1. 1
   workup.ADDITIONAdd, by dropwise addition
2. 2
   workup.ADDITIONadd, by dropwise addition
3. 3
   workup.STIRRINGStir for 30 minutes
4. 4
   workup.STIRRINGStir for 15 minutes
5. 5
   温度to warm to -10° C
6. 6
   workup.STIRRINGStir for 15 minutes
7. 7
   その他Separate the organic phase
8. 8
   洗浄wash with brine
9. 9
   乾燥dry (MgSO4)
10. 10
    その他evaporate the solvent in vacuo
11. 11
    その他Purify by chromatography (ethyl acetate)

実験手順

Dissolve oxalyl chloride (1.57 g, 12.4 mmol) in methylene chloride (17 mL), cool to -55° C. and place under a nitrogen atmosphere. Add, by dropwise addition, a solution of dimethylsulfoxide (1.77 g, 1.61 mL) in methylene chloride (4.5 mL). Stir for 15 minutes and add, by dropwise addition, a solution of 4-[4-[4-(hydroxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-2,2-dimethylphenethyl alcohol (5.0 g, 10.3 mol) in methylene chloride (33 mL). Stir for 30 minutes and add, by dropwise addition, triethylamine (7.2 mL) . Stir for 15 minutes and then allow to warm to -10° C. Add a solution of oxone (12.66 g) in deionized water (50 mL ). Stir for 15 minutes and add methylene chloride (25 mL). Separate the organic phase, wash with brine, dry (MgSO4) and evaporate the solvent in vacuo. Purify by chromatography (ethyl acetate) to give 4-[4-[4-(hydoxydiphenylmethyl)-1-piperidinyl]-1-oxobutyl]-α,α-dimethylbenzeneacetaldehyde.

出典