2-Methylbenzenesulfonic acid → HCID 20041420, compound

HRID 1762530Notes

Reaction equation

HRID 1762530 reaction equation
[CH2:1]([C:4]1([OH:10])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1)[C:2]#[CH:3].[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>CCOCC.C1(C)C(S(O)(=O)=O)=CC=CC=1.C(Cl)(Cl)Cl>[O:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[O:10][C:4]1([CH2:1][C:2]#[CH:3])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5]1

Participants

8

Reactant 4

HCID 69252-Methylbenzenesulfonic acidHCID 80803,4-dihydro-2H-pyran3×HCID 11430Potassium CarbonateHCID 879381-(2-Propynyl)cyclohexan-1-ol

Product 1

HCID 20041420HCID 20041420, compoundYield 98.5%

Reagents, catalysts & solvents 3

HCID 69252-Methylbenzenesulfonic acidCatalyst2×HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

A solution of 2.9 g (21 mmol) of (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 about 5 mg of toluenesulfonic acid. After one hour, tlc (CHCl3, silica gel) analysis indicated that significant starting material remained. Another 0.2 ml of dihydropyran and about 5 mg of toluenesulfonic acid were added. Twice more at one hour intervals, 0.2 ml portions of dihydropyran along with a small amount of toluenesulfonic acid were added to the reaction mixture. It was 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 3300 cm-1.

Workup

  1. additionwas added
  2. waitIt was 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-a1a0452219d04eb1b1a0c713d1e9892d
Source dataset
uspto-grants-1989_05
Patent number
US04833157

Reaction notes

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