Tetrahydrofuran → 5-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1-hydroxyethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881889Notes

Reaction equation

HRID 1881889 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:13](=[O:16])[CH:14]=[CH2:15])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[OH:24][CH:25]([C:27]1[S:31][C:30]([CH:32]=[O:33])=[N:29][CH:28]=1)[CH3:26].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:13](=[O:16])[CH2:14][CH2:15][C:32]([C:30]2[S:31][C:27]([CH:25]([OH:24])[CH3:26])=[CH:28][N:29]=2)=[O:33])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:9])=[O:10]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593312984-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593313835-(1-Hydroxyethyl)-1,3-thiazole-2-carbaldehyde

Product 1

HCID 593313595-[3-chloro-4-(methylsulfonyl)phenyl]-1-[5-(1-hydroxyethyl)-1,3-thiazol-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 81.8%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-[3-chloro-4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.56 g), 5-(1-hydroxyethyl)-1,3-thiazole-2-carbaldehyde (0.30 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (43 mg), triethylamine (0.09 mL), tetrahydrofuran (4 mL) and ethanol (4 mL) was stirred with heating under reflux for 3 hr. The reaction mixture was concentrated, the residue was subjected to basic silica gel column chromatography, and eluted with ethyl acetate, and the fraction was concentrated. The residue was subjected to silica gel column chromatography, and the title compound (0.66 g, yield 81%) was obtained as a pale-yellow oil from a fraction eluted with ethyl acetate. MS: 514 (MH+).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 3 hr
  3. concentrationThe reaction mixture was concentrated
  4. washeluted with ethyl acetate
  5. concentrationthe fraction was concentrated

Sources & evidence

ORD record
ord-0bd6fc809dd64896bbd5a1d9a501a7f6
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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