Dimethyl Sulfoxide → HCID 60026693, compound

HRID 400654Notes

Reaction equation

HRID 400654 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][C:20]=1[C:27]([CH3:32])([CH3:31])[CH2:28][CH2:29][OH:30])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.O>ClCCl>[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([S:25][CH3:26])=[CH:21][C:20]=1[C:27]([CH3:32])([CH3:31])[CH2:28][CH:29]=[O:30])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 962WaterHCID 65578Oxalyl chlorideHCID 60026317HCID 60026317, compound

Product 1

HCID 60026693HCID 60026693, compoundYield 78.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 1.57 mL of oxalyl chloride in 15 mL of dichloromethane at −60° C. was added a solution of 2.55 mL of DMSO in 5 mL of dichloromethane. After 10 minutes, a solution of 3-(2-benzyloxy-5-methylsulfanylphenyl)-3-methylbutan-1-ol (2.84 g, 8.9 mmol) in 5 mL of dichloromethane was added (solids quickly precipitated), followed 15 minutes later by 7.5 mL triethylamine and the reaction mixture became very thick with solids. The reaction mixture was then warmed to room temperature and monitored by TLC. After 1 hour, TLC of an aliquot showed reaction was complete, so water was added to the reaction mixture and the resulting layers were separated. The aqueous layer was washed with dichloromethane and the organics were combined, washed four times with water, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford a yellow oil. The residue was purified on SiO2 (0% to 10% ethyl acetate-hexanes) to give 2.2 g (78.7% yield) of 3-(2-benzyloxy-5-methylsulfanylphenyl)-3-methylbutyraldehyde as a colorless oil that slowly crystallized upon standing.

Workup

  1. customquickly precipitated),
  2. waitfollowed 15 minutes later by 7.5 mL triethylamine
  3. waitAfter 1 hour
  4. customreaction
  5. additionwas added to the reaction mixture
  6. customthe resulting layers were separated
  7. washThe aqueous layer was washed with dichloromethane
  8. washwashed four times with water
  9. washwashed with brine
  10. dry with materialdried over magnesium sulfate
  11. concentrationconcentrated in vacuo
  12. customto afford a yellow oil
  13. customThe residue was purified on SiO2 (0% to 10% ethyl acetate-hexanes)

Sources & evidence

ORD record
ord-f78510be733a45f1a7b5de826ceeb0e6
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

Loading…