Dimethyl Sulfoxide → HCID 86748933, compound

HRID 1757263Notes

Reaction equation

HRID 1757263 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.C(Cl)Cl.[CH3:14][C:15]([CH3:45])([CH3:44])[C:16]#[C:17]/[CH:18]=[CH:19]/[CH2:20][CH:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[CH:34]=2)[CH:26]=1)[CH2:22][OH:23]>CCCCCC.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:14][C:15]([CH3:45])([CH3:44])[C:16]#[C:17][CH:18]=[CH:19][CH2:20][CH:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27](/[CH:31]=[CH:32]/[C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]3[CH:43]=[CH:42][S:41][CH:40]=3)[CH:34]=2)[CH:26]=1)[CH:22]=[O:23]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 15288604HCID 15288604, compound

Product 1

HCID 86748933HCID 86748933, compoundYield 73.3%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
-78 °C

Procedure

44 μl of oxalyl chloride is added dropwise to a mixture of 3.6 μl of dimethyl sulfoxide with 2 μl of methylene chloride under a nitrogen atmosphere and under cooling at -78° C. and stirring, and the mixture is stirred at that temperature for 10 minutes. A methylene chloride solution (0.4 ml) of 105 mg of (E,E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-3-[3-[2-[3-(3-thienyl)phenyl]ethenyl]phenyl]propanol obtained in Example 12 is added dropwise to this solution under cooling at -78° C. and stirring, the mixture is stirred at that temperature for 20 minutes, 200 μl of triethylamine is added, and the mixture is further stirred at -78° C. for 20 minutes. The solvent is distilled off under reduced pressure, the residue is led to two liquid phases using a system of water and ethyl ether, the organic layer is washed with saturated saline and dried over anhydrous magnesium sulfate, and then the solvent is distilled off under reduced pressure. The residue is purified by medium pressure liquid chromatography [column: Lobar column: size A, Lichroprep Si 60F (produced by Merck Co.); eluent: hexane/ethyl acetate=20/1] to obtain 76.6 mg (yield: 73%) of (E)-2-(6,6-dimethyl-2-hepten-4-ynyl)-3-[3-[2-[3-(3-thienyl)phenyl]ethenyl]phenyl]propionaldehyde as a colorless oily matter.

Workup

  1. stirringthe mixture is stirred at that temperature for 10 minutes
  2. temperatureunder cooling at -78° C.
  3. stirringstirring
  4. stirringthe mixture is stirred at that temperature for 20 minutes
  5. stirringthe mixture is further stirred at -78° C. for 20 minutes
  6. distillationThe solvent is distilled off under reduced pressure
  7. washthe organic layer is washed with saturated saline
  8. dry with materialdried over anhydrous magnesium sulfate
  9. distillationthe solvent is distilled off under reduced pressure
  10. customThe residue is purified by medium pressure liquid chromatography [column

Sources & evidence

ORD record
ord-85934d5836a94dcf8c2c5134215ffd86
Source dataset
uspto-grants-1995_08
Patent number
US05444084

Reaction notes

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