Tetrahydrofuran → 1-{5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridin-2-yl}-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881900Notes

Reaction equation

HRID 1881900 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([CH:11]([CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[C:12](=[O:15])[CH:13]=[CH2:14])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:23][O:24][CH2:25][CH:26]([C:34]1[CH:35]=[CH:36][C:37]([CH:40]=[O:41])=[N:38][CH:39]=1)[O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1.C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH3:23][O:24][CH2:25][CH:26]([C:34]1[CH:35]=[CH:36][C:37]([C:40](=[O:41])[CH2:14][CH2:13][C:12](=[O:15])[CH:11]([C:8]2[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=2)[CH2:16][CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[N:38][CH:39]=1)[O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593314795-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridine-2-carbaldehydeHCID 684337694-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one

Product 1

HCID 593313111-{5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridin-2-yl}-5-[4-(methylsulfonyl)phenyl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 54%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-[4-(methylsulfonyl)phenyl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (1.07 g), 5-[2-methoxy-1-(tetrahydro-2H-pyran-2-yloxy)ethyl]pyridine-2-carbaldehyde (0.97 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (90 mg), triethylamine (0.23 mL), tetrahydrofuran (8 mL) and ethanol (8 mL) was stirred with heating under reflux for 1 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography, and the title compound (1.05 g, yield 54%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (2:1, volume ratio). MS: 588 (MH+).

Workup

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

Sources & evidence

ORD record
ord-56a484180513465ab9cdc86340694d81
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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