Dimethyl Sulfoxide → HCID 59463779, compound

HRID 1713348Notes

Reaction equation

HRID 1713348 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[F:11][C:12]([F:30])([F:29])[CH:13]([OH:28])[CH2:14][C:15]1([CH3:27])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([S:25][CH3:26])[CH:23]=2)[O:18][CH2:17][CH2:16]1.C(N(CC)CC)C>C(Cl)Cl>[F:30][C:12]([F:11])([F:29])[C:13](=[O:28])[CH2:14][C:15]1([CH3:27])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([S:25][CH3:26])[CH:23]=2)[O:18][CH2:17][CH2:16]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 59463781HCID 59463781, compound

Product 1

HCID 59463779HCID 59463779, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a chilled (−60° C.) solution of 0.254 mL (2.9 mmol) of oxalyl chloride in 5 mL of methylene chloride was added a solution of 0.414 mL (7 mmol) of DMSO in 2.5 mL of dichloromethane. After 10 minutes, a solution of 450 mg (1.46 mmol) of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-ol in 2.5 mL of dichloromethane was added. The mixture stirred for 15 minuets and then 1.2 mL (8.7 mmol) of triethylamine was added. The reaction was warmed to 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 340 mg (94%) of 1,1,1-trifluoro-3-(4-methyl-6-methylsulfanylchroman-4-yl)propan-2-one 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-bd8ca28ddd9d4330b00c60cbdb3a4c94
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

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