Ethanol → 1-[5-(1,2-Bis{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-6-cyclopentyl-5-[5-(methylsulfanyl)pyridin-2-yl]hexane-1,4-dione

HRID 1881948Notes

Reaction equation

HRID 1881948 reaction equation
[CH:1]1([CH2:6][CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=2)[C:8](=[O:11])[CH:9]=[CH2:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(O)C.O1CCCC1.[Si:28]([O:35][CH:36]([C:46]1[CH:47]=[CH:48][C:49]([CH:52]=[O:53])=[N:50][CH:51]=1)[CH2:37][O:38][Si:39]([C:42]([CH3:45])([CH3:44])[CH3:43])([CH3:41])[CH3:40])([C:31]([CH3:34])([CH3:33])[CH3:32])([CH3:30])[CH3:29]>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(OCC)(=O)C.C(N(CC)CC)C>[Si:28]([O:35][CH:36]([C:46]1[CH:47]=[CH:48][C:49]([C:52](=[O:53])[CH2:10][CH2:9][C:8](=[O:11])[CH:7]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][N:13]=2)[CH2:6][CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5]2)=[N:50][CH:51]=1)[CH2:37][O:38][Si:39]([C:42]([CH3:44])([CH3:45])[CH3:43])([CH3:41])[CH3:40])([C:31]([CH3:32])([CH3:33])[CH3:34])([CH3:30])[CH3:29]

Participants

8

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 593315425-Cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-oneHCID 593316215-(1,2-Bis{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde

Product 1

HCID 593314141-[5-(1,2-Bis{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridin-2-yl]-6-cyclopentyl-5-[5-(methylsulfanyl)pyridin-2-yl]hexane-1,4-dioneYield 60.3%

Reagents, catalysts & solvents 3

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

Procedure

To a solution of 5-cyclopentyl-4-[5-(methylsulfanyl)pyridin-2-yl]pent-1-en-3-one (464 mg) in a mixed solvent of ethanol (8 mL) and tetrahydrofuran (8 mL) were added 5-(1,2-bis{[tert-butyl(dimethyl)silyl]oxy}ethyl)pyridine-2-carbaldehyde (1.07 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (45.3 mg) and triethylamine (93.7 μL), and the mixture was stirred with heating under reflux for 1 hr. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with water. The ethyl acetate layer was dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and the title compound (682 mg, yield 60%) was obtained as a pale-yellow amorphous solid from a fraction eluted with ethyl acetate-hexane (1:4, volume ratio).

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr
  3. washwashed with water
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-31012b01addc48e5a95767f0f1639ba3
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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