Tetrahydrofuran → Diphenylphosphine oxide

847 μl (10.2 mmol) of diphenylphosphine in 16 ml of abs. THF was deprotonated at -10° with 3.05 ml nBuLi (1.5M, hexane). The solution was then cooled to -75° and 2.76 g (4.15 mmol) of (Z)-(3S,5S)-1-(2-chloro-ethylidene)-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohexane, dissolved in 16 ml of abs. THF, was added dropwise. 10 Minutes later, 190 μl of water was injected and the reaction mixture allowed to reach room temperature. All solvents were then removed i.V., the residue taken up in 33 ml of CH2Cl2 and treated with 81 ml of 5% H2O2. After stirring for 75 minutes, the layers were separated, the queous phase extracted with AcOEt, the organic layers washed with sodium pyrosulfite, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/AcOEt=45/55) afforded 2.534 g of (Z)-(3S,5S)-[2 t-3,5-bis-(tert-butyl-diphenyl-silanyloxy)-2-methylene-cyclohexylidene]-ethyl]-diphenyl-phosphine oxide as colorless foam.

1. temperatureThe solution was then cooled to -75°
2. customto reach room temperature
3. customAll solvents were then removed i.V
4. additiontreated with 81 ml of 5% H2O2
5. customthe layers were separated
6. extractionthe queous phase extracted with AcOEt
7. washthe organic layers washed with sodium pyrosulfite
8. dry with materialdried over sodium sulfate
9. customevaporated to dryness

ORD record

ord-3df07772e552425eb761d27564668148

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05919986