Dimethyl Sulfoxide → Diethyl 5-(4-fluorobenzoyl)-1,3-benzenedipropanoate

HRID 53329Notes

Reaction equation

HRID 53329 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[F:11][C:12]1[CH:17]=[CH:16][C:15]([CH:18]([OH:39])[C:19]2[CH:20]=[C:21]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:22]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=2)=[CH:14][CH:13]=1.C(N(CC)CC)C>ClCCl>[F:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:19]2[CH:20]=[C:21]([CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH:22]=[C:23]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:24]=2)=[O:39])=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19962357Diethyl 5-[(4-fluorophenyl)hydroxymethyl]-1,3-benzenedipropanoate

Product 1

HCID 19962378Diethyl 5-(4-fluorobenzoyl)-1,3-benzenedipropanoateYield 94.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulphoxide (16.2 ml) was added dropwise to a stirred solution of oxalyl chloride (11.55 g) in dry dichloromethane (500 ml) at -78° C. under an atmosphere of dry nitrogen. The mixture was stirred for 10 minutes and then a solution of diethyl 5-[(4-fluorophenyl)hydroxymethyl]-1,3-benzenedipropanoate (30.65 g) in dry dichloromethane (150 ml) was added dropwise. The mixture was stirred at -78° C. for 30 minutes, triethylamine (23.03 g) was added, and stirring was continued for a further 10 minutes. The temperature was allowed to rise to room temperature, and the mixture was washed with water. The organic layer was separated, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel. Elution with dichloromethane followed by dichloromethane/methanol (50:1) gave the title compound as an oil (28.92 g), Rf 0.75 (SS 4). Found: C,69.08; H,6.46. C23H25FO5 requires: C,68.98; H,6.29%.

Workup

  1. stirringThe mixture was stirred at -78° C. for 30 minutes
  2. stirringstirring
  3. waitwas continued for a further 10 minutes
  4. customto rise to room temperature
  5. washthe mixture was washed with water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. customevaporated
  9. customThe residue was chromatographed on silica gel
  10. washElution with dichloromethane

Sources & evidence

ORD record
ord-7fd4f784084343b086d6fb22b205e37a
Source dataset
uspto-grants-1997_04
Patent number
US05618941

Reaction notes

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