57586-92-2

Usage

Synthesis Reference(s)

Synthetic Communications, 14, p. 179, 1984 DOI: 10.1080/00397918408062821

InChI:InChI=1/C19H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-14-17-20-19-16-13-15-18-21-19/h3-4,19H,2,5-18H2,1H3/b4-3+

Upstream product

• 50816-20-1 2-(8-bromooctyloxy)tetrahydropyran 
• 63281-96-9 (E)-1-bromo-3-hexene 
• 7611-87-2 1(E)-chloro-1-butene 
• 917-54-4 methyllithium 
• 76063-05-3 1-mesyloxy-13-tetrahydropyranyloxy-2(E)-tridecene 
• 57586-82-0 [1-((E)-Propenyl)-11-(tetrahydro-pyran-2-yloxy)-undecyl]-phosphonic acid diethyl ester 
• 1577-18-0 (E)-3-hexenoic acid 
• 928-97-2 (E)-3-hexen-1-ol 
• 69157-16-0 3(E)-hexenoic-ethanoic anhydride 
• 51795-88-1 1-bromo-10-(tetrahydropyranyloxy)decane 
• 112-43-6 10-Undecen-1-ol 
• 10160-25-5 7-bromo-1-(2-tetrahydropyranyloxy)heptane 
• 31502-26-8 (E)-1-bromo-hept-4-ene 
• 24469-79-2 (E)-hept-4-en-1-ol 

Downstream Products

• 33189-72-9 (E)-tetradec-11-en-1-yl acetate 
• 35746-21-5 E,Z-11-tetradecen-1-al 
• 35153-18-5 (E)-11-tetradecen-1-ol 

Relevant academic research and scientific papers

Stereoselective synthesis of 11(E)-tetradecen-1-yl acetate-Sex pheromone of sod webworm (Loxostege sticticalis)

On the basic of Claisen rearrangement using orthoesters we carried out stereoselective synthesis of 11(E)-tetradecen-1-yl acetate, a sex pheromone of sod webworm (Loxostege sticticalis), which is a specially dangerous pests of crops.

SYNTHESIS OF(E) AND (Z) ALKENES VIA PALLADIUM OR NICKEL-CATALYZED REACTION OF VINYL CHLORIDES WITH GRIGNARD REAGENTS.

We herein described (i) a useful transformation of (E) and (Z) vinyl chlorides into E (and Z) olefins and (ii) an efficient preparation of monoenic alcohols or acetates and its application to insect pheromones.

Synthesis of (E)-11-Tetradecen-1-ol

Protection of alcoholic function of the alcohol (II) as its tetrahydropyranyl ether gives III which on hydroboration-oxidation reaction affords 11-tetrahydropyranyloxyundecanol (IV).Oxidation of IV with pyridinium chlorochromate in anhyd. methylene chloride yields the corresponding aldehyde (V) which when subjected to modified Wittig reaction with ethyl diethylphosphonoacetate furnishes ethyl 13-tetrahydropyranyloxy-2(E)-tridecenoate (VI).LAH reduction of VI in dry benzene affords the alcohol (VII) in good yield.Conversion of the alcohol (VII) into the corresponding mesylate (VIII) with mesyl chloride/triethylamine in dry methylene chloride at 0 deg C, followed by reaction with dimethyl lithiocuprate at -10 deg C under nitrogen atmosphere provides the pyranyl ether (IX) which upon removal of the protective group with conc.HCl in methanol gives the naturally occurring sex pheromone (E)-11-tetradecen-1-ol (I).