3,4-dihydro-2H-pyran → 2H-Pyran, tetrahydro-2-[(3-methyl-3-butenyl)oxy]-

HRID 1195634Notes

Reaction equation

HRID 1195634 reaction equation
[CH:1]([OH:6])=[CH:2][C:3](=[CH2:5])[CH3:4].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C>C(Cl)Cl.CS(O)(=O)=O>[CH3:5][C:3](=[CH2:4])[CH2:2][CH2:1][O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 8471TriethylamineHCID 71353452HCID 71353452, compound

Product 1

HCID 122906552H-Pyran, tetrahydro-2-[(3-methyl-3-butenyl)oxy]-Yield 100.5%

Reagents, catalysts & solvents 2

HCID 6395Methanesulfonic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To isoprenyl alcohol (80.0 g, 929 mmol) in CH2Cl2 (500 ml) at 0° C. was added one drop of methanesulfonic acid. To this solution was added 2,3-dihydropyran (100 ml, 1.10 mol) dropwise over 3 h. After the addition was complete triethylamine (5 ml) was added and the resulting mixture was filtered through a thin pad of SiO2 and concentrated to afford 159 g (100%) of 2-(3-methyl-3-butenyloxy)tetrahydropyran as a colorless liquid.

Workup

  1. additionAfter the addition
  2. additionwas added
  3. filtrationthe resulting mixture was filtered through a thin pad of SiO2
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-d0beb8aeaabb4b1095ae2b8dbb94e40e
Source dataset
uspto-grants-1992_05
Patent number
US05112595

Reaction notes

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