Dimethyl Sulfoxide → HCID 52916043, compound

HRID 559066Notes

Reaction equation

HRID 559066 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH2:8][O:9][C:10]([CH2:12][C:13]([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])=[O:14])=[O:11].[C:21](=S)=[S:22].CI.[CH3:26][S:27]([CH3:29])=O>>[CH2:19]([O:18][C:16](=[O:17])[C:15](=[C:26]([S:22][CH3:21])[S:27][CH3:29])[C:13](=[O:14])[CH2:12][C:10]([O:9][CH2:8][CH3:7])=[O:11])[CH3:20]

Participants

6

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 11430Potassium CarbonateHCID 66045Diethyl acetonedicarboxylate

Product 1

HCID 52916043HCID 52916043, compoundYield 26%

Conditions

Temperature
5 °C

Procedure

Potassium carbonate (34.15 g, 247 mmol) was slowly added to a solution of diethyl 1,3-acetone dicarboxylate (50 g, 247 mmol) in anhydrous DMSO (64 mL) at room temperature The reaction mixture was stirred for 30 minutes and was cooled to 5° C. Carbon disulfide (14.92 mL, 247 mmol) was added dropwise over 30 minutes at 5-10° C., followed by stirring at 0° C. for 1 h. Methyl iodide (30.8 mL, 494 mmol) was then added dropwise at 10° C. and the reaction mixture was stirred at this temperature for 1 h. After quenching the reaction with water, it was extracted with DCM. The combined organics extracts were dried (MgSO4) and concentrated under reduced pressure. Purification by silica gel (1:7 EtOAc/hexanes) gave 20.2 g (26%) of the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 4.18 (q, 2H), 4.08 (q, 2H), 3.71 (s, 2H), 2.45 (s, 6H), 1.23 (t, 3H), 1.18 (t, 3H). MS (ES) [m+H] calc'd for C11H8F4O3, 307; found 307.

Workup

  1. stirringby stirring at 0° C. for 1 h
  2. stirringthe reaction mixture was stirred at this temperature for 1 h
  3. customAfter quenching
  4. customthe reaction with water, it
  5. extractionwas extracted with DCM
  6. dry with materialThe combined organics extracts were dried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel (1:7 EtOAc/hexanes)

Sources & evidence

ORD record
ord-4ee438a3536e4897aa58616c52feaa3e
Source dataset
uspto-grants-2011_11
Patent number
US08063066B2

Reaction notes

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