Hydrochloric Acid → 1-Octanol, 8-[(tetrahydro-2H-pyran-2-yl)oxy]-
Reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]CC/C=C/C=C\CCCC)(=O)C.[CH2:20]([OH:29])[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][OH:28].O1C=CCCC1.Cl>ClCCl>[O:4]1[CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[O:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][OH:29]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Procedure
The synthesis of compound I, the major component of the attractant composition of the invention is illustrated in FIG. 1. In brief, 1,8-octanediol is reacted with dihydropyran in dichloromethane catalyzed by hydrochloric acid to give 8-[(tetrahydro-2H-pyran-2-yl)oxy]-1-octanol, which is reacted with pyridinium chlorochromate to give 8-[(tetrahydro-2H-pyran-2-yl)oxy]octanal (A). The octanal (A) is then reacted with diethylcyanomethylphosphate and sodium hydride to produce 10-[(tetrahydro-2H-pyran-2-yl)oxy]-2-decenitrile (B). Diisobutylaluminum hydride reduces the nitrile (B) to an imine which upon hydrolysis yields the aldehyde (C). Wittig coupling of (C) with n-pentyl triphenylphosphorane gives the mixture of conjugated dienes (D) which upon hydrolysis and acetylation give the two isomeric pentadecadien-1-ol acetates (E). The (E,E)-8,10-isomer is removed by Diels-Alder reaction with tetracyanoethylene to give pure (E,Z)-8,10-pentadecadien- 1-ol acetate (I). A detailed description of the synthesis of I is given in Example 4, below.
Sources & evidence
- ORD record
- ord-49c6c9d8866240da89bee59e79d23750
- Source dataset
- uspto-grants-1997_03
- Patent number
- US05607670
Reaction notes
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