(5-Iodopyridin-3-yl)-methanol
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(5-Iodopyridin-3-yl)-methanol

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(5-Iodopyridin-3-yl)-methanol (CAS# 72299-58-2) is a useful research chemical.

Category
Amino Alcohol
Catalog number
BAT-008775
CAS number
72299-58-2
Molecular Formula
C6H6INO
Molecular Weight
235.02
(5-Iodopyridin-3-yl)-methanol
IUPAC Name
(5-iodopyridin-3-yl)methanol
Synonyms
(5-iodopyridin-3-yl)methanol
Purity
95 %
Density
1.982 g/cm3
Boiling Point
333.3 ℃ at 760 mmHg
InChI
InChI=1S/C6H6INO/c7-6-1-5(4-9)2-8-3-6/h1-3,9H,4H2
InChI Key
MAESWHLLEUUMGK-UHFFFAOYSA-N
Canonical SMILES
C1=C(C=NC=C1I)CO
2. Montmorillonite K-10 clay-catalyzed Ferrier rearrangement of 2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol: a few unexpected domino transformations
Elumalai Kumaran, Meenakshisundaram Santhi, Kalpattu K Balasubramanian, Shanmugasundaram Bhagavathy Carbohydr Res. 2011 Sep 27;346(13):1654-61. doi: 10.1016/j.carres.2011.03.027. Epub 2011 Mar 21.
Montmorillonite K-10 clay-catalyzed substitution reactions of 3,4,6-tri-O-alkyl-2-C-hydroxymethyl-d-glycals, 3,4,6-tri-O-acetyl-d-glycals, 3,4,6-tri-O-alkyl-d-glycals, and 3,4-(dihydro-2H-pyran-5-yl)methanol with a few alcohols and phenols are described. The reactions of 2-C-hydroxymethyl-d-glycals with phenols were similar to those of 2-C-acetoxymethyl-d-glycals and afforded pyrano[2,3-b]benzopyrans. This montmorillonite K-10 clay-catalyzed transformation is facile both under ambient (Method 1) and microwave conditions (Method 2). Ferrier rearrangement of 3,4-(dihydro-2H-pyran-5-yl)methanol with p-cresol, 2,6-xylenol, and ethanol led to totally unexpected transformations. Reaction of 2-C-hydroxymethyl-d-galactal with 2,6-dimethylphenol in the presence of montmorillonite K-10 led to a novel domino transformation affording 4-(5',6'-dihydro-4H-pyran-3'-ylmethyl)-2,6-dimethylphenol. In contrast, 3,4,6-tri-O-acetyl-d-glucal furnished the Ferrier rearrangement product, 2,6-dimethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-α-d-erythro-hex-2-enopyranoside. Also, isomerization of 3,4,6-tri-O-alkyl-d-glycals to products of allylic rearrangement, 2,3-unsaturated-O-glycosides in good yields is reported.
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