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

HRID 1881850Notes

Reaction equation

HRID 1881850 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.[OH:34][CH:35]([C:40]1[CH:41]=[CH:42][C:43]([CH:46]=[O:47])=[N:44][CH:45]=1)[C:36]([OH:39])([CH3:38])[CH3:37]>[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:46]([C:43]3[CH:42]=[CH:41][C:40]([CH:35]([OH:34])[C:36]([OH:39])([CH3:37])[CH3:38])=[CH:45][N:44]=3)=[O:47])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehydeHCID 684311882-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)hex-4-en-3-one

Product 1

HCID 593314295-[4-(cyclopropylsulfonyl)phenyl]-1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-2-methyl-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 76.4%

Reagents, catalysts & solvents 3

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

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 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (129 mg), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (16.4 mg) and triethylamine (33.2 μL), and the mixture was stirred with heating under reflux under argon m atmosphere 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 (235 mg, yield 76%) was obtained as a yellow amorphous solid from a fraction eluted with ethyl acetate. MS: 558 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux under argon m atmosphere for 3 hr
  3. washwashed with water
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b78b6f66c6e94bf7847041407066cc7f
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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