Tetrahydrofuran → 1-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dione

HRID 1881894Notes

Reaction equation

HRID 1881894 reaction equation
[CH3:1][S:2][C:3]1[CH:4]=[CH:5][C:6]([CH:9]([CH2:14][CH:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[C:10](=[O:13])[CH:11]=[CH2:12])=[N:7][CH:8]=1.[OH:21][CH:22]([C:27]1[CH:28]=[CH:29][C:30]([CH:33]=[O:34])=[N:31][CH:32]=1)[C:23]([OH:26])([CH3:25])[CH3:24].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[OH:21][CH:22]([C:27]1[CH:28]=[CH:29][C:30]([C:33](=[O:34])[CH2:12][CH2:11][C:10](=[O:13])[CH:9]([C:6]2[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][N:7]=2)[CH2:14][CH:15]2[CH2:16][CH2:17][O:18][CH2:19][CH2:20]2)=[N:31][CH:32]=1)[C:23]([OH:26])([CH3:24])[CH3:25]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 593313384-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-oneHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde

Product 1

HCID 593312671-[5-(1,2-dihydroxy-2-methylpropyl)pyridin-2-yl]-5-[5-(methylsulfanyl)pyridin-2-yl]-6-(tetrahydro-2H-pyran-4-yl)hexane-1,4-dioneYield 63.9%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of 4-[5-(methylsulfanyl)pyridin-2-yl]-5-(tetrahydro-2H-pyran-4-yl)pent-1-en-3-one (0.50 g), 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (0.32 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (43 mg), triethylamine (0.09 mL), tetrahydrofuran (6 mL) and ethanol (6 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 (0.51 g, yield 61%) was obtained as a colorless oil from a fraction eluted with ethyl acetate. MS: 524 (MH+).

Workup

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

Sources & evidence

ORD record
ord-a672bc2f51974601a0b7a9b0a998bad9
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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