Application of piperazine-derived hydrazone linkers for alkylation of solid-phase immobilized ketones

Synlett

Volumn , Issue 11, 2002, Pages 1931-1934

  Lazny, Ryszard ^a   Michalak, Michal ^a  

^a UNIVERSITY OF BIALYSTOK   (Poland)

Author keywords

Alkylations; Hydrazones; Ketones; Lithiation; Solid phase synthesis

Indexed keywords

1 IODOPROPANE; 3 PENTANONE; 4 TERT BUTYLCYCLOHEXANONE; ALKANONE; BENZYL BROMIDE; CYCLOHEXANONE; HYDRAZONE DERIVATIVE; KETONE DERIVATIVE; N AMINOPIPERAZINE; PIPERAZINE; PIPERAZINE DERIVATIVE; POLYMER; PROPANE; TROPANONE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL BINDING; CHEMICAL REACTION; IMMOBILIZATION; LITHIATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0036423666     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2002-34879     Document Type: Article

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23. 3 aq and KOH aq to decompose the grey suspension of LAH. The resulting white precipitate was dissolved and removed by washing with 2 M HCl aq. The resin was washed with a mixture of concd HCl and THF (4.5:5.5, 2 × 10 mL), repeatedly with THF, methanol, dichloromethane followed by 10% (v/v) solution of triethylamine in dichloromethane (3 × 8 mL, under argon) and repeatedly with methanol and dichloromethane. The resulting resin was dried under high vacuum to constant mass (2.130 g, 93%).
24. 3N·HCl and t-butylcyclohexanone were usually in good agreement.
25. 3, dried, and concentrated under moderate vacuum to give crystalline solid (0.045 g, 0.58 mmol/g).
26. 4) and concentrated to give 2-propylcyclohexanone (0.038 g, 92%).
27. 13C NMR spectroscopy