Methylenetriphenylphosphorane → HCID 18790897, compound

HRID 1005261Notes

Reaction equation

HRID 1005261 reaction equation
[CH2:1]([CH:5]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][O:13][Si:14]([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15])[CH:6]=O)[CH2:2][CH2:3][CH3:4].[CH2:21]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.C1COCC1.CCCCCC>[Si:14]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH:5]([CH2:1][CH2:2][CH2:3][CH3:4])[CH:6]=[CH2:21])([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 137960MethylenetriphenylphosphoraneHCID 18790891HCID 18790891, compound

Product 1

HCID 18790897HCID 18790897, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21883165Tetrahydrofuran hexaneSolvent

Procedure

2-Butyl-7-(tert-butyldimethylsilyloxy)heptanaI (6.01 g, 20 mmol) in 15 ml of anhydrous THF was added dropwise to a freshly prepared solution of methylidene(triphenyl)phosphorane (22 mmol in 125 ml of anhydrous THF/hexane at 0° C. over a period of 15 min. The mixture was warmed to room temperature, stirred for 8 h, and poured into 300 ml of ice/water and extracted (3×75 ml) with ether. The combined organic extracts were washed with water and dried over anhydrous MgSO4. Solvents were removed by evaporation and pentane (250 ml) was added to the red oily residue. The mixture was chilled to 0° C. and the precipitated Ph3PO removed by filtration The precipitate was washed with ice-cold pentane and the filtrate concentrated in vacuo. The crude product was purified by PMPLC yielding 4.06 g (68%) of 8-(tert-butyldimethylsilyloxy)-3-butyloct-1-ene.

Workup

  1. extractionextracted (3×75 ml) with ether
  2. washThe combined organic extracts were washed with water
  3. dry with materialdried over anhydrous MgSO4
  4. customSolvents were removed by evaporation and pentane (250 ml)
  5. additionwas added to the red oily residue
  6. temperatureThe mixture was chilled to 0° C.
  7. customthe precipitated Ph3PO removed by filtration The precipitate
  8. washwas washed with ice-cold pentane
  9. concentrationthe filtrate concentrated in vacuo
  10. customThe crude product was purified by PMPLC

Sources & evidence

ORD record
ord-1348dfa4019442d085b986b4f3ec5150
Source dataset
uspto-grants-2000_04
Patent number
US06054141

Reaction notes

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