Triphenylphosphine → HCID 70452497, compound

HRID 2290815Notes

Reaction equation

HRID 2290815 reaction equation
[H-].[Na+].[Br-].[CH2:4]1[CH2:35][O:34][CH2:33][CH:6]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[O:5]1.CC1(CCCCCCCBr)OCCO1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH2:69]([O:76][C:77]1[CH:78]=[C:79]([CH:82]=[CH:83][C:84]=1[O:85][CH2:86][C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1)[CH:80]=O)[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>CS(C)=O.O>[CH2:69]([O:76][C:77]1[CH:78]=[C:79]([CH:80]=[CH:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH:6]2[O:5][CH2:4][CH2:35][O:34][CH2:33]2)[CH:82]=[CH:83][C:84]=1[O:85][CH2:86][C:87]1[CH:92]=[CH:91][CH:90]=[CH:89][CH:88]=1)[C:70]1[CH:71]=[CH:72][CH:73]=[CH:74][CH:75]=1

Participants

9

Reactant 5

HCID 11776TriphenylphosphineHCID 24758Sodium hydrideHCID 795263,4-Bis(benzyloxy)benzaldehydeHCID 19823699HCID 19823699, compoundHCID 86741087HCID 86741087, compound

Product 1

HCID 70452497HCID 70452497, compoundYield 36.6%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideCatalystHCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

A mixture of 640 mg of oily sodium hydride (60%) and 10 mg of dimethyl sulfoxide was stirred for 45 minutes at 75° to 80° C. After cooling the mixture, a mixture of 50 ml of dimethyl sulfoxide and 8.2 g of 8-ethylenedioxynonyl triphenylphosphonium bromide prepared from 2-methyl-2-(7-bromoheptyl)-1,3-dioxolan and triphenylphosphin was added to the mixture. After 10 minutes, a mixture of 2.5 g of 3.4-dibenzyloxybenzaldehyde and 10 ml of dimethyl sulfoxide was added to the mixture at room temperature and the resultant mixture was stirred overnight. To the reaction mixture was added 500 ml of water and the product was extracted with ether. The extract was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to provide an oily product. The product was applied to the silica gel (200 ml) column chromatography and eluted with a mixture of n-hexane and ether (1:1) to provide 1.4 g of 1-(3,4 -dibenzyloxyphenyl)-9-ethylenedioxy-1-decene.

Workup

  1. temperatureAfter cooling the mixture
  2. additionwas added to the mixture
  3. waitAfter 10 minutes
  4. additionwas added to the mixture at room temperature
  5. extractionthe product was extracted with ether
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto provide an oily product
  10. washeluted with a mixture of n-hexane and ether (1:1)

Sources & evidence

ORD record
ord-1919b458b78348788f86ddb58dbfa93d
Source dataset
uspto-grants-1986_10
Patent number
US04618627

Reaction notes

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