메뉴 건너뛰기
Synlett
Volumn , Issue 16, 2008, Pages 2532-2534
An efficient one-pot synthesis of ω-hydroxy ketones from lactones
Author keywords

hydroxy ketones; Lactones; One pot reaction; Weinreb ketone synthesis
Indexed keywords

GRIGNARD REAGENT; KETONE DERIVATIVE; LACTONE DERIVATIVE; TETRAHYDROFURAN;
EID: 54149105742     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1078175     Document Type: Article
Times cited : (15)
References (24)
  • 19
    • 54149094625 scopus 로고    scopus 로고
    • It is worth to note that when phenylmagnesium bromide was used, an unexpected small amount byproduct was obtained. Its structure was identified as 1,4-dihydroxy-1-phenyl-butane. The reaction detail is being studied.
    • It is worth to note that when phenylmagnesium bromide was used, an unexpected small amount byproduct was obtained. Its structure was identified as 1,4-dihydroxy-1-phenyl-butane. The reaction detail is being studied.
  • 22
    • 34247137978 scopus 로고    scopus 로고
    • Beshore, D. C.; Smith, A. B. III J. Am. Chem. Soc. 2007, 129, 4148.
    • (c) Beshore, D. C.; Smith, A. B. III J. Am. Chem. Soc. 2007, 129, 4148.
  • 23
    • 54149096081 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of ω-Hydroxy Ketones from Lactones A slurry of lactone (1.0 mmol, HN(OMe)Me·HCl (116 mg, 1.2 mmol, and NaOMe (14 mg, 0.25 mmol) in THF (20 mL) was cooled with an ice-salt bath under nitrogen. A solution of Grignard reagent in THF (16 mL, 0.5 M, 8.0 mmol) was added slowly. After 2 h in an ice-salt bath the reaction mixture was allowed to warm to r.t. and stirred for 8 h. The reaction was quenched with 1 N HCl solution (10 mL, The mixture was stirred for another 2 h, and THF was evaporated. The residue was treated with H2O (20 mL) and then extracted with CH2Cl2. The organic extract was dried over MgSO4 and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc-PE) to give the desired hydroxy ketone
    • 4 and concentrated. The residue was purified by flash column chromatography on silica gel (EtOAc-PE) to give the desired hydroxy ketone.
  • 24
    • 54149118146 scopus 로고    scopus 로고
    • +], 183 (0.3), 141 (1.3).
    • +], 183 (0.3), 141 (1.3).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.