An efficient catalyst-free regio- and stereoselective ring-opening of epoxides with phenoxides using polyethylene glycol as the reaction medium

Tetrahedron Letters

Volumn 48, Issue 24, 2007, Pages 4263-4265

  Das, Biswanath ^a   Krishnaiah, Maddeboina ^a   Thirupathi, Ponnaboina ^a   Laxminarayana, Keetha ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

Aryloxyalcohols; Catalyst free conversion; Epoxide; PEG 400; Regio and stereoselectivity

Indexed keywords

EPOXIDE; MACROGOL; PHENOXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYST; CHEMICAL REACTION; RING OPENING; ROOM TEMPERATURE; STEREOCHEMISTRY;

EID: 34248547201     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.062     Document Type: Article

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17. General experimental procedure: To the suspension of an epoxide (1 mmol) in PEG (2 g), the phenoxide (1.1 mmol) was added and the mixture was stirred at room temperature. The reaction was monitored by TLC. After completion, the mixture was poured onto water and extracted with EtOAc (3 × 10 mL). The extract was concentrated and the residue was subjected to column chromatography (silica gel, ethyl acetate-hexane 2:8) to obtain the pure β-aryloxyalcohol. The PEG was recovered from the water and recycled without affecting the yields of the products.