Réaction #81619

Équation de réaction

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

Solvants

water

triethylamine

methylene chloride

methylene chloride

methylene chloride

methylene chloride

Conditions de réaction

Traitement

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
   Températureto warm to -10° C
6. 6
   workup.STIRRINGStir for 15 minutes
7. 7
   AutreSeparate the organic phase
8. 8
   Lavagewash with brine
9. 9
   Séchagedry (MgSO4)
10. 10
    Autreevaporate the solvent in vacuo
11. 11
    AutrePurify by chromatography (ethyl acetate)

Mode opératoire

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.

Source