Dimethyl Sulfoxide → HCID 21883599, compound

HRID 722304Notes

Reaction equation

HRID 722304 reaction equation
[Cl:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[C:4]([CH:11]=[O:12])[CH:3]=1.CS(C)=O.[F:17][C:18]([F:27])([F:26])/[CH:19]=[CH:20]/[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(N(CC)CC)C>C(OCC)C.CCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:11]=[O:12])[C:5]2[O:10][CH:19]([C:18]([F:17])([F:27])[F:26])[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:7][C:6]=2[CH:9]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 1229125-Chloro-2-hydroxyisophthalaldehydeHCID 5371261Ethyl (2E)-4,4,4-trifluoro-2-butenoate

Product 1

HCID 21883599HCID 21883599, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
80 °C

Procedure

A stirred solution of the dialdehyde (Step 2) (1.13 g, 6.14 mmol), dimethyl sulfoxide (6 mL), ethyl 4,4,4-trifluorocrotonate (1.37 mL, 1.55 g, 9.21 mmoL) and triethylamine (1.71 mL, 1.24 g, 12.28 mmol) in a round bottom flask fitted with condenser was heated to 80° C. for 8 h. Upon cooling to room temperature the reaction was diluted with diethyl ether (100 mL) and the resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL), dried over MgSO4, filtered and concentrated in vacuo yielding a tan powder. This powder was taken up in hot hexane-ethyl acetate and filtered to remove insoluble matter. Upon cooling of the filtrate, crystallization followed by vacuum filtration yielded the desired ester as tan crystals (0.726 g, 35%): mp 118.1–119.7° C. This material was of suitable purity to use without further purification.

Workup

  1. temperatureUpon cooling to room temperature the reaction
  2. washthe resulting mixture washed with aqueous sodium bicarbonate solution (3×75 mL), 1 N HCl solution (3×70 mL), and brine (1×75 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customyielding a tan powder
  7. filtrationfiltered
  8. customto remove insoluble matter
  9. temperatureUpon cooling of the filtrate, crystallization
  10. filtrationfollowed by vacuum filtration

Sources & evidence

ORD record
ord-b83320cb706b45c3823c139ca43ab160
Source dataset
uspto-grants-2006_11
Patent number
US07138411B2

Reaction notes

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