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Volumn , Issue 17, 2008, Pages 2629-2632

Synthesis and reactions of the first fluorine-containing 1,3-bis(trimethylsilyloxy)-1,3-butadienes

(7) Adeel, Muhammad a Reim, Stefanie a Wolf, Verena a Yawer, Mirza A a Hussain, Ibrar a Villinger, Alexander a Langer, Peter a

a UNIVERSITY OF ROSTOCK (Germany)

Author keywords

Arenes; Organofluorine compounds; Regioselectivity; Silyl enol ethers

Indexed keywords

1,3 BIS (TRIMETHYLSILOXY) 1,3 BUTADIENE DERIVATIVE; 1,3 BIS(SILYL ENOL ETHER DERIVATIVE); 1,3 BUTADIENE DERIVATIVE; ETHER DERIVATIVE; FLUORINE DERIVATIVE; ORGANOFLUORINE DERIVATIVE; PYRIDINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELECTROPHILIC STRESS; SYNTHESIS;

EID: 55449123315 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-0028-1083440 Document Type: Article

Times cited : (11)

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- CCDC 684861 contains the supplementary crystallographic data for this paper
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50
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- Synthesis of 2-Ethoxy-3-fluoro-6-(phenylsulfonyl)pyridin-4-ol (14, To phenylsulfonyl cyanide was dropwise added 3a at -78 °C. The neat reaction mixture was subsequently stirred at 45 °C for 48 h. To the mixture was added a sat. aq solution of NH4Cl (20 mL) and the organic and the aqueous layer were separated. The latter was extracted with CH 2Cl2 (3 × 20 mL, The combined organic layers were dried (Na2SO4, filtered and the filtrate was concentrated in vacuo. The residue was purified by chromatography (silica gel, heptanes-EtOAc) to give 14. Starting with phenylsulfonyl cyanide (0.167 g, 1.0 mmol) and 3a (0.589 g, 2.0 mmol, 14 was isolated as a red solid (0.179 g, 59, 1H NMR (250 MHz, CDCl3, δ, 1.22 (t, 3J, 7.1 Hz, 3 H, OCH2CH3, 4.26 (q, 3J, 7.0 Hz, 2 H, OCH2CH3, 7.19 br s, 1 H, OHhet
- 4SNa: 320.03652; found: 320.03633. All products gave satisfactory spectroscopic data and correct elemental analyses and/or high resolution mass data.

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