HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Dimethyl Sulfoxide → 2,6-Diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarbaldehyde

HRID 1709657
Notes
Print preview

Reaction equation

HRID 1709657 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:23]([CH2:24][OH:25])=[C:22]([CH:26]([CH3:28])[CH3:27])[N:21]=[C:20]([CH:29]([CH3:31])[CH3:30])[C:19]=2[CH2:32][OH:33])=[CH:14][CH:13]=1>CS(C)=O.ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[C:19]([CH:32]=[O:33])=[C:20]([CH:29]([CH3:31])[CH3:30])[N:21]=[C:22]([CH:26]([CH3:28])[CH3:27])[C:23]=2[CH:24]=[O:25])=[CH:14][CH:13]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 159242263,5-Dihydroxymethyl-2,6-diisopropyl-4-(4-fluorophenyl)pyridine

Product 1

HCID 159242272,6-Diisopropyl-4-(4-fluorophenyl)-pyridine-3,5-dicarbaldehyde

Reagents, catalysts & solvents 1

HCID 21912085Dimethylsulfoxide-dichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To solution of 16 ml (0.18 mol) oxalyl chloride in 150 ml dry diohloromethans was added, et -78° C., 40 ml dimethyl sulfoxide over a period of 5 minutes. After 10 minutes, 26 g (0,082 mol) of the product of step 3 in 200 ml of 1:3 solution dimethyl sulfoxide/dichloromethane was added dropwise. This reaction mixture was stirred at -78° C. for 20 minutes, before it was quenched with 80 ml triethylamime. The cooling bath was removed and the reaction was allowed to warm to room temperature. The reaction was partitioned between ethyl acetate (500 ml) and 1N hydrochloric acid (200 ml). The organic layer was washed With water (4×100 ml) and brine and dried over magnesium sulfate and filtered. Evaporation of the filtrate in vaouo gave 24.5 g of the Step 4 title product as a viscous oil which was used without further purification.

Workup

  1. additionwas added
  2. customwas quenched with 80 ml triethylamime
  3. customThe cooling bath was removed
  4. temperatureto warm to room temperature
  5. customThe reaction was partitioned between ethyl acetate (500 ml) and 1N hydrochloric acid (200 ml)
  6. washThe organic layer was washed With water (4×100 ml) and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customEvaporation of the filtrate in vaouo

Sources & evidence

ORD record
ord-a2ebfaefbce645b4962cc580c1e81772
Source dataset
uspto-grants-1990_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04950675

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes