Diethyl Ether → HCID 20041420, compound

HRID 1649191Notes

Reaction equation

HRID 1649191 reaction equation
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[C:7]1([CH3:17])[C:8](S(O)(=O)=O)=[CH:9][CH:10]=[CH:11][CH:12]=1.C(Cl)(Cl)Cl.C(=O)([O-])[O-:23].[K+].[K+].[CH3:28][CH2:29]OCC>>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:23][C:7]1([CH2:17][C:28]#[CH:29])[CH2:8][CH2:9][CH2:10][CH2:11][CH2:12]1

Participants

6

Reactant 5

HCID 3283Diethyl EtherHCID 6212ChloroformHCID 69252-Methylbenzenesulfonic acid3×HCID 80803,4-dihydro-2H-pyran3×HCID 11430Potassium Carbonate

Product 1

HCID 20041420HCID 20041420, compound

Procedure

A solution of 2.9 g (21 mmol) of 1RS-(prop-2-ynyl)cyclohexanol in 10 ml of dry ether was stirred under argon as 0.24 ml (26 mmol) of dihydropyran was added followed by a small scoop (ca. 5 mg) of toluenesulfonic acid. After one hour tlc (CHCl3, silica gel) analysis indicated that significant starting material remained so another 0.2 ml of dihydropyran and a small scoop of toluenesulfonic acid were added. Twice more at one hour intervals 0.2 ml portions of dihydropyran and a trace of toluenesulfonic acid were added to the reaction mixture. It was finally left to stir under argon at room temperature for 15 hours. Potassium carbonate was then added to the mixture and it was stirred for several minutes before it was washed with water. The wash solution was back extracted with ether and the combined extracts were then washed with brine, dried (Na2SO4) and evaporated in vacuo to yield 4.6 g of 1-(tetrahydropyran-2-yloxy)-1-(prop-2-ynyl)cyclohexane having the following spectral characteristics: nmr (CDCl3) δ 1.0-2.5 (19H, m), 3.6 (2H, broad m) and 4.65 ppm (1H, broad s); ir (CHCl3) 980, 1030, 1050, 1070, 1120, 1150, 1270, 1450, 2120, (weak), 2760, 2930, and 3330 cm-1.

Workup

  1. additionwas added
  2. waitIt was finally left
  3. stirringwas stirred for several minutes before it
  4. washwas washed with water
  5. extractionThe wash solution was back extracted with ether
  6. washthe combined extracts were then washed with brine
  7. dry with materialdried (Na2SO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-0fa0eac277544f8ca398a6dd67ed5b04
Source dataset
uspto-grants-1983_11
Patent number
US04415592

Reaction notes

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