Dimethyl Sulfoxide → HCID 12080541, compound

HRID 1355636Notes

Reaction equation

HRID 1355636 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Cl:11][C:12]1[S:16][C:15]([CH2:17][C:18]2([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1.CCN(CC)CC.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:11][C:12]1[S:16][C:15]([CH2:17][C:18]2([CH:22]=[O:23])[CH2:21][CH2:20][CH2:19]2)=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 12080540HCID 12080540, compound

Product 1

HCID 12080541HCID 12080541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
23 °C

Procedure

Oxalyl chloride (12 mL, 24 mmol) was added to CH2Cl2 (250 mL) at −78° C. DMSO (3.75 g, 48 mmol) was added dropwise to the mixture and stirring was continued for 15 min. A solution of alcohol 20 (2.57 g, 12 mmol) in CH2Cl2 (20mL) was then added dropwise. After 1 hr at −78° C., Et3N (9.72 g, 96 mmol) was added and the mixture was warmed to 23° C. After 1 h, the mixture was poured into NaHCO3 (sat) and the organic layer was seperated. The aqueous layer was extracted with CH2Cl2 (2×) and the combined organic layer was washed with brine, dried (Na2SO4), concentrated and purified by FCC (silica gel, 100% hexane; 2:1, hexane/CH2Cl2) to afford the above named aldehyde 21.

Workup

  1. waitAfter 1 hr at −78° C.
  2. waitAfter 1 h
  3. customthe organic layer was seperated
  4. extractionThe aqueous layer was extracted with CH2Cl2 (2×)
  5. washthe combined organic layer was washed with brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. custompurified by FCC (silica gel, 100% hexane; 2:1, hexane/CH2Cl2)

Sources & evidence

ORD record
ord-56e51e121dd746d9abc223e4cc246f20
Source dataset
uspto-grants-2003_07
Patent number
US06586462B2

Reaction notes

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