Tetrahydrofuran → HCID 53656365, compound

HRID 461939Notes

Reaction equation

HRID 461939 reaction equation
[CH3:1][Si:2]([CH3:14])([CH3:13])[C:3]#[C:4][CH2:5][O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1.O1CCCC1.C([Li])CCC.[CH3:25][C:26](=O)[CH2:27][CH2:28][CH2:29][CH3:30]>CCCCCC.[I-].[Zn+2].[I-].O>[CH3:14][Si:2]([CH3:13])([CH3:1])[C:3]#[C:4][CH:5]([O:6][CH:7]1[CH2:12][CH2:11][CH2:10][CH2:9][O:8]1)[CH:26]([CH3:25])[CH2:27][CH2:28][CH2:29][CH3:30]

Participants

8

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 115832-HexanoneHCID 107037813-TETRAHYDROPYRANYLOXY-1-TRIMETHYLSILYL-1-PROPYNEHCID 178418339Butyllithium

Product 1

HCID 53656365HCID 53656365, compound

Reagents, catalysts & solvents 3

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

To 13.6 parts of the above ether in 100 parts by volume of tetrahydrofuran at -70° C is added 37 parts by volume of 2.4 molar butyl lithium in hexane. This mixture is stirred for 20 minutes at -70° C and the solution is allowed to stand for 45 minutes and then 17.8 parts of zinc iodide in 350 parts by volume of tetrahydrofuran is added while maintaining the temperature at -70° C. The resulting yellow solution is stirred for 1 hour and 8 parts of 2-hexanone in 50 parts by volume of tetrahydrofuran is added while retaining the temperature at -70° C. The reaction mixture is allowed to warm to -30° C, water is carefully added, and the reaction mixture is allowed to come to room temperature. The reaction mixture is extracted with ether, washed with water and saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent is stripped and the residual oil is distilled at 107°-110° C/0.5 mm to provide 1-trimethylsilyl-3-tetrahydropyranyloxy-4-methyl-1-octyne.

Workup

  1. waitto stand for 45 minutes
  2. temperaturewhile maintaining the temperature at -70° C
  3. stirringThe resulting yellow solution is stirred for 1 hour
  4. customat -70° C
  5. temperatureto warm to -30° C
  6. customto come to room temperature
  7. extractionThe reaction mixture is extracted with ether
  8. washwashed with water and saturated sodium chloride
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationthe residual oil is distilled at 107°-110° C/0.5 mm

Sources & evidence

ORD record
ord-e39054f18b10421fadd51a0105c6c8e2
Source dataset
uspto-grants-1977_12
Patent number
US04064350

Reaction notes

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