Dimethyl Sulfoxide → HCID 58377416, compound

HRID 2068667Notes

Reaction equation

HRID 2068667 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([C:16]1([CH2:22][OH:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1)[CH2:12][CH2:13][CH2:14][CH3:15]>C(Cl)Cl>[CH2:11]([C:16]1([CH:22]=[O:23])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:12][CH2:13][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 573169791318951-91-5

Product 1

HCID 58377416HCID 58377416, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

DMSO (930 L) was added to a −78° C. solution of oxalyl chloride (3.2 mL, 2 M/toluene) in CH2Cl2 (44 mL). After 15 min., a solution of alcohol 2-3 (968 mg, 5.3 mmol) in 14 mL CH2Cl2 was added by cannula, rinsing with 2 mL CH2Cl2. The reaction was stirred for 15 min. and Et3N (5.9 mL) was added. The reaction was allowed to warm to 0° C. and after 2 h, 100 mL saturated NaHCO3 solution was added. The resulting mixture was extracted with CH2Cl2 (3×) and the combined CH2Cl2 solution was washed with H2O and brine and then was dried (Na2SO4), filtered and evaporated to give the title compound.

Workup

  1. washrinsing with 2 mL CH2Cl2
  2. additionEt3N (5.9 mL) was added
  3. addition100 mL saturated NaHCO3 solution was added
  4. extractionThe resulting mixture was extracted with CH2Cl2 (3×)
  5. washthe combined CH2Cl2 solution was washed with H2O and brine
  6. dry with materialwas dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-a44310b272624867bdaaa94baf7c9b2f
Source dataset
uspto-grants-2012_10
Patent number
US08299068B2

Reaction notes

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