3,4-dihydro-2H-pyran → 2-[(4,4-Dimethyloct-1-YN-3-YL)oxy]oxane

HRID 225358Notes

Reaction equation

HRID 225358 reaction equation
[CH3:1][C:2]([CH3:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH:3]([OH:6])[C:4]#[CH:5].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>P(Cl)(Cl)(Cl)=O.C(N(CC)CC)C>[CH3:1][C:2]([CH3:11])([CH2:7][CH2:8][CH2:9][CH3:10])[CH:3]([O:6][CH:13]1[CH2:14][CH2:15][CH2:16][CH2:17][O:12]1)[C:4]#[CH:5]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 145163694,4-Dimethyl-1-octyn-3-ol

Product 1

HCID 145163702-[(4,4-Dimethyloct-1-YN-3-YL)oxy]oxane

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 24813Phosphorus oxychlorideCatalyst

Procedure

To a solution of 23.1 g. (0.150 mole) of 4,4-dimethyl-1-octyn-3-ol (Example 149) in 126 g. of freshly distilled dihydropyran is added 1 drop of phosphorus oxychloride and the solution is maintained at ambient temperature in a tightly stoppered flask for 20 hours. Five drops of triethylamine are then added and the mixture is evaporated in vacuo to an oil. The oil is chromatographed on 600 g. of silica gel and the product is eluted with 5% ethyl acetate in benzene yielding a colorless oil.

Workup

  1. customthe mixture is evaporated in vacuo to an oil
  2. customThe oil is chromatographed on 600 g
  3. washof silica gel and the product is eluted with 5% ethyl acetate in benzene yielding a colorless oil

Sources & evidence

ORD record
ord-8780e8d28d93486494bc8f93693a19c5
Source dataset
uspto-grants-1980_11
Patent number
US04236027

Reaction notes

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