Dimethyl Sulfoxide → HCID 59463783, compound

HRID 1713346Notes

Reaction equation

HRID 1713346 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[CH3:11][C:12]1([CH2:24][CH2:25][OH:26])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([S:22][CH3:23])[CH:20]=2)[O:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C(Cl)Cl>[CH3:11][C:12]1([CH2:24][CH:25]=[O:26])[C:21]2[C:16](=[CH:17][CH:18]=[C:19]([S:22][CH3:23])[CH:20]=2)[O:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59463789HCID 59463789, compound

Product 1

HCID 59463783HCID 59463783, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a chilled (−60° C.) solution of 0.31 mL (3.5 mmol) of oxalyl chloride in 5 μL of methylene chloride was added a solution of 0.5 mL (7 mmol) of DMSO in 2.5 mL of dichloromethane. After 10 minutes, a solution of 0.42 g (1.76 mmol) of 2-(4-methyl-6-methylsulfanylchroman-4-yl)ethanol in 2.5 mL of dichloromethane was added. The mixture stirred for 15 minutes and then 1.5 mL (10.6 mmol) of triethylamine was added. The reaction was warmed at room temperature for 30 minutes and then concentrated in vacuo. The residue was diluted with water and extracted with diethyl ether. The combined organic fractions were washed with four portions of water, once with brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 0.4 g (94%) of (4-methyl-6-methylsulfanylchroman-4-yl)acetaldehyde as an oil.

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted with diethyl ether
  4. washThe combined organic fractions were washed with four portions of water, once with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1a76836cf60405faf746e727e21972c
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

Loading…