Methyl vinyl ketone → HCID 10776658, compound

HRID 1189582Notes

Reaction equation

HRID 1189582 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.C(N(CC)CC)C.[CH3:20][C:21](=[O:24])[CH:22]=[CH2:23]>C(O)C.[Br-].C([N+]1C(C)=C(CCO)SC=1)C>[F:1][C:2]([F:11])([F:12])[C:3]1[CH:10]=[CH:9][C:6]([C:7](=[O:8])[CH2:23][CH2:22][C:21](=[O:24])[CH3:20])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 6570Methyl vinyl ketoneHCID 8471TriethylamineHCID 679964-(Trifluoromethyl)benzaldehyde

Product 1

HCID 10776658HCID 10776658, compoundYield 59.2%

Reagents, catalysts & solvents 2

HCID 99649233-Ethyl-5-(2-hydroxyethyl)-4-methylthiazolium bromideCatalystHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

In a small vial charged with 4-(trifluoromethyl)benzaldehyde (3.00 mL, 21.98 mmol) in Ethanol (Volume: 9.5 mL) was added triethylamine (6.13 mL, 44.0 mmol), but-3-en-2-one (2 mL, 21.98 mmol), and 3-ethyl-5-(2-hydroxyethyl)-4-methylthiazol-3-ium bromide (1.109 g, 4.40 mmol). The reaction mixture was heated at 80° C. for 16 h and then concentrated. The residue was treated with 1N HCl and extracted with DCM (3×). The organic layer was dried with MgSO4. The crude product was added to an 80 g ISCO silica gel column and was purified with a gradient of 0% to 40% EtOAc/hexanes. The product was obtained as a colorless crystalline solid (3.18 g, 13.02 mmol, 59.2% yield). 1H NMR (CDCl3/400 MHz) δ (ppm) 8.07 (d, 2H), 7.71 (d, 2H), 3.26 (t, 2H), 2.91 (t, 2H), 2.25 (s, 3H); MS m/z: 245.18 (M+1).

Workup

  1. concentrationconcentrated
  2. additionThe residue was treated with 1N HCl
  3. extractionextracted with DCM (3×)
  4. dry with materialThe organic layer was dried with MgSO4
  5. additionThe crude product was added to an 80 g ISCO silica gel column
  6. customwas purified with a gradient of 0% to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-bb4cd1a34f244604b739f4fdbb30af35
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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