The betaine-ylide route to trans-alkenols

(E)-RCH:CH(CH2)nOH (n = 2,3,5,7; R = Et, pentyl, hexyl, E-CH:CHMe) were obtained in 69-78% yield in a 1-pot reaction by treating HO(CH2)nCH2P+Ph3 Br- with PhLi in tetrahydrofuran-EtiO, followed by addn. of RCHO, treatment with HCl-Et2O, and with KOCMe3. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 26, 3, 311-14
Year:
1985
Keywords:
Note:
CAN 103:6068
26-2
Biomolecules and Their Synthetic Analogs
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
66-25-1; 111-71-7; 123-38-6; 123-73-9 Role: RCT (Reactant), RACT (Reactant or reagent) (Wittig reaction of, with hydroxyalkylidene phosphoranes); 10339-60-3P; 10339-62-5P; 31502-19-9P; 42513-42-8P; 89995-99-3P; 96854-18-1P; 96854-19-2P; 96854-20-5P Role: RCT (Reactant), PREP (Preparation), RACT (Reactant or reagent) (formation and Wittig reaction of, with aldehydes); 96854-21-6P; 96854-22-7P; 96854-23-8P; 96881-36-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of); 51860-45-8; 65734-62-5; 68760-65-6; 87436-78-0 Role: PROC (Process) (ylide formation of, with phenyllithium)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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