Lithium amide → 2-[(8-Methylnon-2-YN-1-YL)oxy]oxane

HRID 1414593Notes

Reaction equation

HRID 1414593 reaction equation
[C:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)#[C:2][CH3:3].[NH2-].[Li+].[CH3:13][CH:14]([CH3:20])[CH2:15][CH2:16][CH2:17][CH2:18]Br>CS(C)=O>[O:6]1[CH2:7][CH2:8][CH2:9][CH2:10][CH:5]1[O:4][CH2:1][C:2]#[C:3][CH2:18][CH2:17][CH2:16][CH2:15][CH:14]([CH3:20])[CH3:13]

Participants

5

Reactant 3

HCID 24532Lithium amideHCID 5207261-Bromo-5-methylhexaneHCID 214687462-Propynyloxytetrahydropyran

Product 1

HCID 681175012-[(8-Methylnon-2-YN-1-YL)oxy]oxane

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

(0.5 mole) of prop-1-ynyltetrahydropyranyl ether in 200 ml of dimethyl sulfoxide were added with stirring to a solution of 11.5g. (0.5 mole) of lithium amide in 200 ml of dimethyl sulfoxide. Stirring was continued for 1 hour and 5-methylhexyl bromide 89g. (0.5 mole) were added over 45 min. External cooling was necessary to keep the temperature at 30° C. After 3 hours, the mixture was poured into 1 liter of ice-water. The mixture was extracted with petrol-ether, and the organic phase washed with 10% sulfuric acid, and then water. The solution was dryed over magnesium sulfate concentrated and distilled at 100°-103° C/0.01mm to give 82.6 (70%) of 8-methylnon-2-ynyl tetrahydropyranyl ether.

Workup

  1. stirringStirring
  2. addition(0.5 mole) were added over 45 min
  3. temperatureExternal cooling
  4. customat 30° C
  5. waitAfter 3 hours
  6. extractionThe mixture was extracted with petrol-ether
  7. washthe organic phase washed with 10% sulfuric acid
  8. concentrationconcentrated
  9. distillationdistilled at 100°-103° C/0.01mm

Sources & evidence

ORD record
ord-32d45820a2db42bd8127c144879b1b86
Source dataset
uspto-grants-1977_01
Patent number
US04001454

Reaction notes

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