Tetrahydrofuran → HCID 59331428, compound

HRID 1881903Notes

Reaction equation

HRID 1881903 reaction equation
[CH:1]1([S:4]([C:7]2[CH:12]=[CH:11][C:10](/[C:13](/[C:21](=[O:24])[CH:22]=[CH2:23])=[CH: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.[OH:25][CH:26]([C:31]1[CH:32]=[CH:33][C:34]([CH:37]=[O:38])=[N:35][CH:36]=1)[C:27]([OH:30])([CH3:29])[CH3:28].C(N(CC)CC)C.O1CCCC1>[Cl-].C([N+]1C(C)=C(CCO)SC=1)C1C=CC=CC=1.C(O)C>[CH:1]1([S:4]([C:7]2[CH:8]=[CH:9][C:10](/[C:13](=[CH:14]\[CH:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)/[C:21](=[O:24])[CH2:22][CH2:23][C:37]([C:34]3[CH:33]=[CH:32][C:31]([CH:26]([OH:25])[C:27]([OH:30])([CH3:28])[CH3:29])=[CH:36][N:35]=3)=[O:38])=[CH:11][CH:12]=2)(=[O:6])=[O:5])[CH2:2][CH2:3]1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 59331469HCID 59331469, compoundHCID 593314885-(1,2-Dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde

Product 1

HCID 59331428HCID 59331428, compoundYield 79%

Reagents, catalysts & solvents 2

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

Procedure

A mixture of (1E)-2-[4-(cyclopropylsulfonyl)phenyl]-1-(tetrahydro-2H-pyran-4-yl)penta-1,4-dien-3-one (4.16 g), 5-(1,2-dihydroxy-2-methylpropyl)pyridine-2-carbaldehyde (2.58 g), 3-benzyl-5-(2-hydroxyethyl)-4-methyl-1,3-thiazol-3-ium chloride (0.32 g), triethylamine (0.84 mL), tetrahydrofuran (10 mL) and ethanol (10 mL) was stirred with heating under reflux for 2 hr. The reaction mixture was concentrated, and the residue was subjected to basic silica gel column chromatography, and the title compound (0.70 g, yield 79%) was obtained as yellow crystals from a fraction eluted with ethyl acetate. melting point 102-104° C.

Workup

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

Sources & evidence

ORD record
ord-6f9b46904efe4c8fac1dc207595d662a
Source dataset
uspto-grants-2012_11
Patent number
US08318746B2

Reaction notes

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