Реакция #81619

Уравнение реакции

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

Растворители

water

triethylamine

methylene chloride

methylene chloride

methylene chloride

methylene chloride

Условия реакции

Обработка

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
   Температураto warm to -10° C
6. 6
   workup.STIRRINGStir for 15 minutes
7. 7
   ДругоеSeparate the organic phase
8. 8
   Промывкаwash with brine
9. 9
   Сушкаdry (MgSO4)
10. 10
    Другоеevaporate the solvent in vacuo
11. 11
    ДругоеPurify by chromatography (ethyl acetate)

Методика

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.

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