Ethanol → HCID 59331402, compound

HRID 1882121Notes

Reaction equation

HRID 1882121 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:12](=O)[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[C:23]([O:27][CH2:28][CH3:29])(=[O:26])[CH:24]=O.C([N:32](CC)CC)C.C(O)C>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.O1CCCC1>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:12]2[NH:32][C:24]([C:23]([O:27][CH2:28][CH3:29])=[O:26])=[CH:14][CH:13]=2)[CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:7][CH:6]=1)(=[O:4])=[O:3]

Participants

7

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 70211Ethyl oxoacetateHCID 684337694-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 59331402HCID 59331402, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a mixture of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (350 mg), ethyl glyoxylate (polymer type, 47% toluene solution) (260 mg), triethylamine (0.31 mL), ethanol (15 mL) and tetrahydrofuran (5 mL) was added 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (280 mg) and the mixture was heated under reflux for 1 hr under argon atmosphere. The reaction mixture was concentrated, water was added to the residue and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. A mixture of the obtained residue, ammonium acetate (1.36 g) and acetic acid (10 mL) was stirred at 120° C. for 2 hr. The reaction mixture was concentrated, saturated aqueous sodium hydrogen carbonate solution was added to the residue, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (140 mg, yield 31%) was obtained as a pale-brown oil from a fraction eluted with hexane-ethyl acetate (1:1-1:2, volume ratio). MS: 406 (MH+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hr under argon atmosphere
  3. concentrationThe reaction mixture was concentrated
  4. additionwater was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. washThe ethyl acetate layer was washed with saturated brine
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. additionA mixture of the obtained residue, ammonium acetate (1.36 g) and acetic acid (10 mL)
  10. concentrationThe reaction mixture was concentrated
  11. additionsaturated aqueous sodium hydrogen carbonate solution was added to the residue
  12. extractionthe mixture was extracted with ethyl acetate
  13. washThe ethyl acetate layer was washed with saturated brine
  14. dry with materialdried (MgSO4)
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-40f5ad1c55a04fd784dd3270b87397cd
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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