Water → 3-TETRAHYDROPYRANYLOXY-1-TRIMETHYLSILYL-1-PROPYNE

HRID 461938Notes

Reaction equation

HRID 461938 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[CH:10].C([Li])CCC.[CH3:16][Si:17](Cl)([CH3:19])[CH3:18].O>CCOCC.CCCCCC>[CH3:16][Si:17]([CH3:19])([CH3:18])[C:10]#[C:9][CH2:8][O:7][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1

Participants

7

Reactant 4

HCID 962WaterHCID 6397ChlorotrimethylsilaneHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 178418339Butyllithium

Product 1

HCID 107037813-TETRAHYDROPYRANYLOXY-1-TRIMETHYLSILYL-1-PROPYNE

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-50 °C

Procedure

To 24.4 parts of 3-tetrahydropyranyloxy-1-propyne dissolved in 300 parts by volume of anhydrous ether and cooled to -50° C is added 74 parts by volume of 2.4 molar n-butyl lithium in hexane. The mixture is stirred for 45 minutes and allowed to warm to 30° C and then 19.3 parts of trimethylsilyl chloride in 50 parts by volume of dry ether is added and the mixture allowed to stand for about 12 hours. The mixture is cooled to 5° C and water is added. The ethereal layer is washed with water, saturated sodium chloride, and dried over anhydrous sodium sulfate. The solvent is removed and the residual liquid is distilled at 0.20 mm at 67°-69° to provide 1-trimethylsilyl-3-tetrahydropyranyloxy-1-propyne (Tetrahedron 29, 883 (1973).

Workup

  1. temperatureto warm to 30° C
  2. waitto stand for about 12 hours
  3. temperatureThe mixture is cooled to 5° C
  4. washThe ethereal layer is washed with water, saturated sodium chloride
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent is removed
  7. distillationthe residual liquid is distilled at 0.20 mm at 67°-69°

Sources & evidence

ORD record
ord-0079c95a40a14d57b443494777009992
Source dataset
uspto-grants-1977_12
Patent number
US04064350

Reaction notes

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