Dimethyl Sulfoxide → (E)-3-[6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolyl]propenal

HRID 34296Notes

Reaction equation

HRID 34296 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH3:22])[C:16]([CH2:23]/[CH:24]=[CH:25]/[OH:26])=[C:15]2[C:27]1[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=1.C(N(CC)CC)C>ClCCl>[Cl:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH3:22])[C:16](/[CH:23]=[CH:24]/[CH:25]=[O:26])=[C:15]2[C:27]1[CH:28]=[CH:29][C:30]([F:33])=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 20129396(E)-3-[6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolyl]-propenol

Product 1

HCID 14229331(E)-3-[6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolyl]propenal

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of oxalyl chloride (2.28 mL, 1.3 equivalents) in 100 mL of dichloromethane was cooled to -78° C. under a nitrogen atmosphere. A solution of dimethylsulfoxide (3.67 mL, 2.6 equivalents) in 75 mL of dichloromethane was added dropwise with stirring. Five minutes after addition was complete, a solution of (E)-3-[6-chloro-4-(4-fluorophenyl)-2-methyl-3-quinolyl]-propenol (6.59 g) in 75 mL of dichloromethane was added dropwise. This solution was stirred at -78° C. for three-quarters of an hour and then 1mL (5.0 equivalents) of triethylamine was added.

Workup

  1. additionFive minutes after addition
  2. stirringThis solution was stirred at -78° C. for three-quarters of an hour

Sources & evidence

ORD record
ord-eb8057b1d32e419097d0311eb70b7227
Source dataset
uspto-grants-1988_08
Patent number
US04761419

Reaction notes

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