Dimethyl Sulfoxide → HCID 86586557, compound

HRID 50011Notes

Reaction equation

HRID 50011 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1([CH2:21][OH:22])[CH2:19][CH2:18][CH:17]1[CH3:20].CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[S:11]1[CH:15]=[CH:14][CH:13]=[C:12]1[C:16]1([CH:21]=[O:22])[CH2:19][CH2:18][CH:17]1[CH3:20]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 69468650HCID 69468650, compound

Product 1

HCID 86586557HCID 86586557, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Oxalyl chloride (50 mL, 0.10 mmol) was added to CH2Cl2 (150 mL) at 23° C. and was cooled to −78° C. DMSO (16 g, 0.20 mmol) was added dropwise to the mixture and stirring was continued for 15 min. A solution of alcohol 4 (7.9 g, 0.041 mmol) in CH2Cl2 (50 mL) was then added dropwise, after which Et3N (44 g, 0.44 mmol) was added and the mixture was warmed to 23° C. After 1 h, the mixture was poured into saturated aqueous NaHCO3 and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic portions were washed with brine, dried (Na2SO4), concentrated in vacuo and purified by FCC (silica gel, 100% hexane followed by 2:1 hexane/CH2Cl2) to afford the above named aldehyde 5.

Workup

  1. temperaturethe mixture was warmed to 23° C
  2. waitAfter 1 h
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. washthe combined organic portions were washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. custompurified by FCC (silica gel, 100% hexane followed by 2:1 hexane/CH2Cl2)

Sources & evidence

ORD record
ord-5e2de942aeb1491192c446e5ae5dad4b
Source dataset
uspto-grants-2004_03
Patent number
US06710072B2

Reaction notes

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