Tetrahydrofuran → Rac. benzyl 2,6,10-trimethylundeca-4,8-dien-1yl ether

Temperatur

0 °C

A suspension of 1.52 g. (3.42 mmoles) of isobutyltriphenylphosphonium iodide in 30 ml. of anhydrous tetrahydrofuran was stirred and cooled to 0° C. while 1.55 ml. (3.42 mmoles) of n-butyllithium solution in hexane was added. The resulting red solution was stirred for 10 minutes at room temperature then treated with a solution of rac. E-8-benzyloxy-3,7-dimethyl-4-octenal (0.594 g.; 2.28 mmoles) in 10 ml. of anhydrous tetrahydrofuran. After stirring at room temperature for 30 minutes, the reaction mixture was treated with water and worked up by extraction with hexane as in Example 1. The semi-solid residue was treated with hexane and filtered to remove insoluble material. The filtrate was concentrated in vacuo to give 0.72 g. of yellow oil. This material was chromatographed on 30 g. of silica gel. Elution with 9:1 parts by volume hexane-ether afforded 0.427 g. (62.5%) of an oil. Evaporative distillation yielded rac. benzyl 2,6,10-trimethyl-undeca-4,8-dien-1-yl ether as a colorless liquid, b.p. 110°-115° C. (bath temperature) (0.03 mm Hg.).

1. additionA suspension of 1.52 g
2. stirringAfter stirring at room temperature for 30 minutes
3. extractionworked up by extraction with hexane as in Example 1
4. additionThe semi-solid residue was treated with hexane
5. filtrationfiltered
6. customto remove insoluble material
7. concentrationThe filtrate was concentrated in vacuo
8. customto give 0.72 g
9. customThis material was chromatographed on 30 g
10. washElution with 9:1 parts by volume hexane-ether
11. customafforded 0.427 g
12. distillationEvaporative distillation

ORD-Eintrag

ord-028c5e727c844a84be1fa78e2b13fae6

Quelldatensatz

uspto-grants-1979_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04180682