Hexane → Heptadec-2,4-dien-1-ol tetrahydropyranyl ether

Temperature

0 °C

Tridecyltriphenyl phosphonium bromide (0.3 mole) was dissolved in 900 ml of tetrahydrofuran and cooled to 0° C. in an ice-salt bath while stirring under argon. A 2.2N solution of n-butyllithium in hexane (0.36 mole) was added dropwise over a period of 30 minutes. The mixture was stirred for an additional 20 minutes and then cooled to -70° C. in a dry ice-acetone bath. The 4-hydroxybut-2(E)-ene-1-al tetrahydropyranyl ether (0.3 mole) in 225 ml of tetrahydrofuran was added dropwise over a period of 35 minutes and the mixture stirred for an additional hour at -70° C. The mixture was then poured into 6.25 liters of ether and stirred for 20 minutes. The resulting mixture was filtered through glass fiber filter paper. The filtrate was evaporated and the residue triturated with hexane, filtered and evaporated to give a ~3:1 mixture of trans:cis isomers of the desired compound.

1. stirringThe mixture was stirred for an additional 20 minutes
2. temperaturecooled to -70° C. in a dry ice-acetone bath
3. stirringthe mixture stirred for an additional hour at -70° C
4. stirringstirred for 20 minutes
5. filtrationThe resulting mixture was filtered through glass fiber
6. filtrationfilter paper
7. customThe filtrate was evaporated
8. customthe residue triturated with hexane
9. filtrationfiltered
10. customevaporated
11. customto give
12. additiona ~3:1 mixture of trans

ORD record

ord-fbb26e83b3cc4e7db2fa1c1d0e990b2e

Source dataset

uspto-grants-1988_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04769386