Water → HCID 19385105, compound

HRID 2399988Notes

Reaction equation

HRID 2399988 reaction equation
[CH:1]#[C:2][C:3]#[C:4][CH2:5][CH2:6][CH2:7][CH3:8].CN(P(N(C)C)(N(C)C)=O)C.[CH2:20]([Li])[CH2:21][CH2:22][CH3:23].Br[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37].[OH2:38]>C1COCC1.CCCCCC>[OH:38][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:23][CH2:22][CH2:21][C:20]#[C:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]#[C:1][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][OH:37]

Participants

8

Reactant 5

HCID 962WaterHCID 12679HexamethylphosphoramideHCID 7416311-Bromo-1-undecanolHCID 6427770OctadiyneHCID 178418339Butyllithium

Product 1

HCID 19385105HCID 19385105, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A solution of octadiyne (9.3 ml; 0.07 mol) in dry THF (200 ml) at 0° C. under nitrogen was treated with HMPA (24.38 ml, 0.14 mol) and n-butyllithium (87.61 ml of a 1.6M solution in hexane; 0.14 mol). The resulting solution was left for ten minutes at 0° C. and then treated with a solution of 11-bromoundecanol (47 g, 0.14 mol). The resulting solution was allowed to stir at room temperature for four hours and then heated at reflux overnight, cooled, diluted with water and extracted with ether. The organic layer was washed with water twice, then dried, evaporated and the residue dissolved in methanol (60 ml). This solution was treated with a catalytic amount of toluenesulphonic acid and heated at reflux for ten minutes. On cooling the title compound (37) separated as pale yellow crystals (18.42 g, 59%).

Workup

  1. waitThe resulting solution was left for ten minutes at 0° C.
  2. temperatureheated
  3. temperatureat reflux overnight
  4. temperaturecooled
  5. extractionextracted with ether
  6. washThe organic layer was washed with water twice
  7. customdried
  8. customevaporated
  9. dissolutionthe residue dissolved in methanol (60 ml)
  10. additionThis solution was treated with a catalytic amount of toluenesulphonic acid
  11. temperatureheated
  12. temperatureat reflux for ten minutes
  13. temperatureOn cooling the title compound (37)
  14. customseparated as pale yellow crystals (18.42 g, 59%)

Sources & evidence

ORD record
ord-406e9b221eff4d2c8a25f20810423408
Source dataset
uspto-grants-1995_09
Patent number
US05451691

Reaction notes

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