A simple method for chemoselective phenol alkylation

Tetrahedron Letters

Volumn 48, Issue 41, 2007, Pages 7380-7382

  Liu, Pingli ^a   Huang, Liang ^a   Faul, Margaret M ^a  

^a AMGEN INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOXYLIC ACID; DIPHENYL ETHER DERIVATIVE; PHENOL; PHOSPHONIUM DERIVATIVE; TETRABUTYLPHOSPHONIUM HYDROXIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE;

EID: 34548510330     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.08.030     Document Type: Article

References (21)

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21. 4POH (10 mmol, 2 equiv) in THF (10 mL) was added the alkylating reagent (5 mmol, 1 equiv) at 0 °C. The reaction mixture was allowed to warm to ambient temperature and stirred until complete, as monitored by HPLC. Typical reactions times were 1-3 h using allyl bromide as the alkylating agent, although longer reaction times >48 h were observed using allyl chloride. With benzyl bromide reaction times of 4-24 h were common. Upon reaction completion, the solvent (THF) was removed in vacuo and the aqueous residue acidified with 2N aqueous HCl. The product precipitated out of solution and was isolated by filtration, followed by water wash. The resultant wet cake was dried in an oven under vacuum to give a white solid. Products that were oils were converted to salts prior to isolation (see Supplementary data).