Methyl vinyl sulfone → HCID 21079429, compound

HRID 1375109Notes

Reaction equation

HRID 1375109 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=[O:6])[CH3:5].[CH:8]([S:10]([CH3:13])(=[O:12])=[O:11])=[CH2:9]>C(N(CC)CC)C.N12CCCN=C1CCCCC2.C(O)C>[C:4]([C:3]([C:2](=[O:7])[CH3:1])([CH2:9][CH2:8][S:10]([CH3:13])(=[O:12])=[O:11])[CH2:9][CH2:8][S:10]([CH3:13])(=[O:12])=[O:11])(=[O:6])[CH3:5]

Participants

6

Reactant 2

HCID 19354Methyl vinyl sulfoneHCID 31261Acetylacetone

Product 1

HCID 21079429HCID 21079429, compound

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneCatalystHCID 702EthanolSolvent

Conditions

Temperature
60 °C

Procedure

6 g of 2,4-pentandione and 3 drops of triethyl amine were mixed and 7 g of methyl vinyl sulfone was added dropwise at room temperature. After stirring at 60° C. for 7 hours, 5 drops of 1,8-diazabicyclo-[5.4.0]-undec-7-ene were added and the mixture was stirred at room temperature for 12 hours. The mixture was stirred with 25 ml of ethanol and neutralized after a white solid was precipitated. The mixture was poured into 200 ml of water and ice, and was kept in the refrigerator overnight. The solvent was filtered off, dried and recrystallized from 500 ml of ethanol. 2.9 g of white, long needles of the subject compound was obtained (melting point: 162° C.; purity: >99%; colorless).

Workup

  1. stirringthe mixture was stirred at room temperature for 12 hours
  2. customwas precipitated
  3. additionThe mixture was poured into 200 ml of water and ice
  4. customwas kept in the refrigerator overnight
  5. filtrationThe solvent was filtered off
  6. customdried
  7. customrecrystallized from 500 ml of ethanol
  8. custom2.9 g of white, long needles of the subject compound was obtained (melting point: 162° C.; purity: >99%; colorless)

Sources & evidence

ORD record
ord-d562950ef8644301a2d0886657352036
Source dataset
uspto-grants-2007_01
Patent number
US07166648B2

Reaction notes

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