Tetrahydrofuran → HCID 59331394, compound

HRID 1881902Notes

Reaction equation

HRID 1881902 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH:15]=[CH2:16])=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH:25]([C:27]1[N:28]=[CH:29][N:30]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=1)=[O:26].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:18][CH:19]3[CH2:24][CH2:23][O:22][CH2:21][CH2:20]3)[C:14](=[O:17])[CH2:15][CH2:16][C:25]([C:27]3[N:28]=[CH:29][N:30]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=3)=[O:26])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 23139317HCID 23139317, compoundHCID 593312584-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 59331394HCID 59331394, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 28333523-Benzyl-5-(2-hydroxyethyl)-4-methylthiazolium chlorideCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[4-(cyclopropylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.77 g), ethyl (4-formyl-1H-imidazol-1-yl)acetate (0.45 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (60 mg), triethylamine (0.12 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography, and the title compound (0.90 g, yield 77%) was obtained as a yellow oil from a fraction eluted with ethyl acetate. MS: 531 (Me).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-cbf4b85ac9a549cab7e34faf68fa8705
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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