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

Temperature

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 record

ord-61e70c9781f54da8b7844cf192ca8d79

Source dataset

uspto-grants-1979_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04163021