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

HRID 1709657Notes

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

Participants

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

additionwas added
customwas quenched with 80 ml triethylamime
customThe cooling bath was removed
temperatureto warm to room temperature
customThe reaction was partitioned between ethyl acetate (500 ml) and 1N hydrochloric acid (200 ml)
washThe organic layer was washed With water (4×100 ml) and brine
dry with materialdried over magnesium sulfate
filtrationfiltered
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

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