Water → 2-[3-[3-(1-Adamantyl)-4-tert.butyldimethylsilyloxyphenyl]-allyl]-1,3-dioxane

Temperature

0 °C

33 g (72.1 mmoles) of [2-(1,3-dioxan-2-yl)ethyl] triphenylphosphonium bromide are suspended in 100 ml of THF. The suspension is cooled to 0° C. and 8.5 g (75.6 mmoles) of potassium terbutylate are added in small amounts. The mixture is left to stand until its temperature reaches 20° C. It is then stirred for 1 hour at which point it is cooled to 0° C. There is then slowly added a solution of 3-(1-adamantyl)-4-tert.butyl-dimethylsilyloxybenzaldehyde in 100 ml of TMF. Once the addition has ended, the mixture is left to stand until its temperature reaches ambient temperature at which point it is stirred for 2 hours, then poured into water, and extracted with methylene chloride. The organic phase is decanted, washed with water, dried over MgSO4 and the solvents evaporated. The residue is purified by passage through a silica column (eluant: 50:50 mixture of CH2Cl2 and hexane), yielding 19.4 g (95% yield) of the expected mixture containing more than 90% of isomer Z, and less than 10% of isomer E.

1. waitThe mixture is left
2. customreaches 20° C
3. temperatureis cooled to 0° C
4. additionOnce the addition
5. waitthe mixture is left
6. customreaches ambient temperature at which point it
7. stirringis stirred for 2 hours
8. extractionextracted with methylene chloride
9. customThe organic phase is decanted
10. washwashed with water
11. dry with materialdried over MgSO4
12. customthe solvents evaporated
13. customThe residue is purified by passage through a silica column (eluant: 50:50 mixture of CH2Cl2 and hexane)

ORD record

ord-a95d43c720c2406fabee5ca1808a4a68

Source dataset

uspto-grants-1992_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05124473