Diethyl Ether → HCID 5283269, compound

HRID 1288510Notes

Reaction equation

HRID 1288510 reaction equation
CC[O:3][CH2:4][CH3:5].[C:6]1([CH3:16])[CH:11]=[CH:10][C:9](S(O)(=O)=O)=[CH:8][CH:7]=1>CO>[CH2:9]([C:10]([CH2:11][CH2:6][CH3:16])=[CH:9][CH2:8][CH2:7]/[CH:16]=[CH:6]/[CH2:7][CH2:8][CH2:5][CH2:4][OH:3])[CH2:10][CH3:11]

Participants

4

Reactant 2

HCID 3283Diethyl EtherHCID 6101p-Toluenesulfonic acid

Product 1

HCID 5283269HCID 5283269, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.6 g of diethyl 6-propyl-2,5-nonadienylphosphonate was dissolved in 10 ml. of tetrahydofuran, and an equivalent amount of n-butyl lithium was added at -60° C. in an atmosphere of argon. To this solution was further added 0.56g of 4-butyl iodide-1-tetrahydropyranyl ether. The temperature of the reaction system was gradually elevated to room temperature. The reaction mixture was poured into ice water, and extracted with ether. Concentration of the solvent gave a pale yellow viscous oily substance. The oily product was dissolved in 20 ml. of ether, and reduced with 0.2 g of lithium aluminum hydride to afford 0.5g of 10-propyl-trans-5,9-tridecadiene-1-tetrahydropyranyl ether in a yield of 80%. This ether was treated with a catalytic amount of p-toluenesulfonic acid in methanol to split off the protective group. Thus, there was obtained pure 10-propyl-trans-5,9-tridecadienol in a quantitative yield. The properties of this product were as follows:

Workup

  1. customto split off the protective group

Sources & evidence

ORD record
ord-34ad78a1c4554a48aa49323636dcc057
Source dataset
uspto-grants-1976_10
Patent number
US03988380

Reaction notes

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