Ethanol → 5-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881848Notes

Reaction equation

HRID 1881848 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10]([CH:13]([C:21](=[O:25])[CH:22]=[CH:23][CH3:24])[CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:9][CH:8]=2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.C(O)C.O1CCCC1.[N:34]1[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=1[CH:40]=[O:41]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10]([CH:13]([CH2:14][CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[C:21](=[O:25])[CH2:22][CH:23]([CH3:24])[C:40]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][N:34]=3)=[O:41])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 142732-PyridinecarboxaldehydeHCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

Product 1

HCID 593312695-[4-(cyclopropylsulfonyl)phenyl]-2-methyl-1-(pyridin-2-yl)-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 69.5%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
80 °C

Procedure

To a solution of 2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one (200 mg) in a mixed solvent of ethanol (3 mL) and tetrahydrofuran (3 mL) were added pyridine-2-carbaldehyde (71.0 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (16.0 mg) and triethylamine (33 μL), and the mixture was stirred under argon atmosphere at 80° C. 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 washed with saturated brine, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (180 mg, yield 69%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio). MS: 470 (MH+).

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water
  3. washThe ethyl acetate layer was washed with saturated brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70561e02c20944ffba4043b134cc4b1f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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