Claims
- 1. A method for the preparation of (R,S)-zearalanone dibenzyl ether comprising reacting 4-penten-2-yl 6-(4-pentenyl)-.beta.-resorcylate with 2,3-dimethyl-2-butylborane to give a tertiary alkyl borane that is then reacted with carbon monoxide under super-atmospheric pressure and then with hydrogen peroxide.
- 2. A method for the preparation of (R,S)-zearalanone dibenzyl ether comprising reaction 4-penten-2-yl 6-(4-pentenyl)-.beta.-resorcylate with 2,3-dimethyl-2-butylborane at a temperature in the range 15.degree.C-50.degree.C to give a tertiary alkyl borane that is then reacted with carbon monoxide under super-atmospheric pressure at a temperature in the range 25.degree.C-80.degree.C and then with hydrogen peroxide.
- 3. A method for the chemical synthesis of (R,S)-zearalanone wich comprises the steps of
- a. reacting 5-hexenal with malonic acid to prepare 2,7-octadienoic acid;
- b. reacting 2,7-octadienoic acid with diazomethane to prepare methyl 2,7-octadienoate;
- c. reacting methyl 2,7-octadienoate with the sodium salt of acetoacetic ester in the presence of methanol and sodium methoxide to prepare the sodium salt of methyl 6-(4-pentenyl)-.beta.-dihydro-resorcylate;
- d. reacting the sodium salt of methyl 6-(4-pentenyl)-.beta.-dihydroresorcylate with bromine to prepare methyl 3-bromo-6-(4pentenyl)-.beta.-dihydroresorcylate; -pentenyl)-.beta.
- e. reacting methyl 3-bromo-6-(4-pentenyl)-.beta.-dihydro-resorcylate with sodium ethoxide to prepare ethyl 6-(4-pentenyl)-.beta.-resorcylate;
- f. reacting ethyl 6-(4-pentenyl)-.beta.-resorcylate with benzyl chloride to prepare ethyl 6-(4-pentenyl)-.beta.-resorcylate dibenzyl ether;
- g. reacting ethyl 6-(4-pentenyl)-.beta.-resorcylate dibenzyl ether with the sodium alcoholate of 4penten-2ol to prepare 4-penten-2-yl 6-(pentenyl).beta.-resorcylate dibenzyl ether;
- h. reacting 4-penten-2yl 6-(4-pentenyl)-.beta.-resorcylate with 2,3-dimethyl-2-butyl borane to give a tertiary alkyl borane that is then reacted with carbon monoxide under super-atmospheric pressure and then with hydrogen peroxide to prepare (R,S)-zearalanone dibenzyl ether;
- i. reacting (R,S)-zearalanone dibenzyl ether with hydrogen to prepare (R,S)-zearalanone.
Parent Case Info
This is a division of application Ser. No. 247,414, filed Apr. 25, 1972 now matured to U.S. Pat. No. 3,862,982 issued Jan. 28, 1975.
US Referenced Citations (3)
Divisions (1)
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Number |
Date |
Country |
Parent |
247414 |
Apr 1972 |
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