CAN mediated cyclization of epoxypropyl cinnamyl ethers: A facile stereoselective synthesis of tetrahydropyran derivatives

Tetrahedron Letters

Volumn 45, Issue 11, 2004, Pages 2413-2416

  Nair, Vijay ^a   Balagopal, Lakshmi ^a   Rajan, Roshini ^a   Deepthi, Ani ^a   Mohanan, Kishor ^a   Rath, Nigam P ^b  

^a REGIONAL RESEARCH LABORATORY CSIR   (India)

^b UNIVERSITY OF MISSOURI ST LOUIS   (United States)

Author keywords

CAN; Epoxypropyl cinnamyl ethers; Tetrahydropyran

Indexed keywords

CERIUM AMMONIUM NITRATE; ETHER DERIVATIVE; NITRIC ACID DERIVATIVE; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; CYCLIZATION; INFRARED RADIATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 1242293071     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.075     Document Type: Article

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35. Experimental procedure for the preparation of epoxypropyl alkenyl ethers: Epoxy alcohols were prepared by a routine procedure involving the m-CPBA oxidation of cinnamyl alcohols. A solution of epoxyalcohol (1 mmol) in dry THF was added to a suspension of NaH (2.5 mmol) in dry THF maintained at 5°C. When the evolution of hydrogen was complete, a solution of alkenyl bromide (1.2 mmol) in dry THF was added to it and the reaction mixture was gradually brought to room temperature and stirred overnight. The solvent was evaporated and the crude residue diluted with water (25 mL), and extracted with dichloromethane (3 × 15 mL). The combined extracts were washed with water, brine and dried over anhydrous sodium sulfate. The pure compound was obtained by chromatography on a silica gel column.
36. 3: C, 73.82, H, 7.12, N, 4.30. Found: C, 73.79, H, 7.09, N, 4.27.