Ethanol → HCID 59331602, compound

HRID 1881937Notes

Reaction equation

HRID 1881937 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][O:18]2)[C:12](=[O:15])[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(O)C.O1CCCC1.[N:30]1[CH:35]=[CH:34][CH:33]=[CH:32][C:31]=1[CH:36]=[O:37]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][O:18]2)[C:12](=[O:15])[CH2:13][CH2:14][C:36]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][N:30]=2)=[O:37])=[CH:9][CH:10]=1)(=[O:4])=[O:3]

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 142732-PyridinecarboxaldehydeHCID 59331489HCID 59331489, compound

Product 1

HCID 59331602HCID 59331602, compoundYield 24%

Reagents, catalysts & solvents 3

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydrofuran-2-yl)pent-1-en-3-one (930 mg) in a mixed solvent of ethanol (7.5 mL) and tetrahydrofuran (7.5 mL) were added pyridine-2-carbaldehyde (323 μL), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (89.6 mg) and triethylamine (181 μL), and the mixture was stirred with heating under reflux for 3 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO9) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (302 mg, yield 24%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (19:1, volume ratio). MS: 416 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO9)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-368aefe88bd84371a9e187228eea822f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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