Dimethyl Sulfoxide → HCID 69429952, compound

HRID 1297024Notes

Reaction equation

HRID 1297024 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]1([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH2:19]O)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C.[Cl-].[Na+].C(OP([CH2:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])(OCC)=O)C.[H-].[Na+]>ClCCl.C(OCC)(=O)C.C1COCC1>[C:11]1([CH:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:18][CH:19]=[CH:44][C:45]([O:47][CH2:48][CH3:49])=[O:46])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

11

Reactant 7

HCID 679Dimethyl SulfoxideHCID 5234Sodium Chloride2×HCID 8471TriethylamineHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 299083,3-DiphenylpropanolHCID 65578Oxalyl chloride

Product 1

HCID 69429952HCID 69429952, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.37 g (18.7 mmol) of oxalyl chloride and 2.92 g (37.3 mmol) of DMSO were dissolved in 10 ml of dichloromethane at −78° C. After stirring for one hour, 2.00 g (9.33 mmol) of 3,3-diphenyl-1-propanol was added to the obtained solution at that temperature, and they were stirred for additional 2 hours. 5.66 g (56.0 mmol) of triethylamine was added to the obtained mixture and they were stirred for one hour while the temperature was returned to room temperature. After the dilution with dichloromethane followed by the washing with saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was added to a THF solution obtained by stirring 2.67 g (11.9 mmol) of ethyl diethylphosphonoacetate and 596 mg (14.9 mmol) of sodium hydride (60% oily) under cooling with ice for one hour. They were stirred at room temperature for 2 hours. After the dilution with ethyl acetate followed by the washing with saturated aqueous sodium chloride solution, the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue thus obtained was purified by the silica gel chromatography (hexane/ethyl acetate=5/1 to 3/1) to obtain the title compound.

Workup

  1. stirringwere stirred for additional 2 hours
  2. stirringwere stirred for one hour while the temperature
  3. customwas returned to room temperature
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue thus obtained
  7. customobtained
  8. temperatureunder cooling with ice for one hour
  9. stirringThey were stirred at room temperature for 2 hours
  10. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  11. concentrationconcentrated under reduced pressure
  12. customThe residue thus obtained
  13. customwas purified by the silica gel chromatography (hexane/ethyl acetate=5/1 to 3/1)

Sources & evidence

ORD record
ord-ef1c68f326ba48d090d33ede07e2bd2e
Source dataset
uspto-grants-2007_07
Patent number
US07247645B2

Reaction notes

Loading…