3,4-dihydro-2H-pyran → 3-Methyl-4-(tetrahydropyran-2-yloxy)-1-butene

HRID 2051728Notes

Reaction equation

HRID 2051728 reaction equation
[CH3:1][CH:2]([CH:5]=[CH2:6])[CH2:3][OH:4].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1>CCOCC.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][CH:2]([CH2:3][O:4][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)[CH:5]=[CH2:6]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 942922-Methyl-3-buten-1-ol

Product 1

HCID 156250113-Methyl-4-(tetrahydropyran-2-yloxy)-1-buteneYield 75.3%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-methyl-3-buten-1-ol (54.16 g, 0.63 m), dihydropyran (52.92 g, 0.63 m), and p-toluenesulfonic acid (0.5 g) in ether (800 ml) is stirred at room temperature under a nitrogen atmosphere overnight. The reaction mixture is then diluted with ether (1 l) and washed with 5% sodium bicarbonate solution (1 l). The ether extract is dried (Na2SO4), filtered and solvent removed in vacuo to give 95.8 g of crude product. The crude product is purified by column chromatography on silica gel (500 g, hexane) to give (75%) 3-methyl-4-(tetrahydropyran-2-yloxy)-1-butene (80.62 g).

Workup

  1. washwashed with 5% sodium bicarbonate solution (1 l)
  2. extractionThe ether extract
  3. dry with materialis dried (Na2SO4)
  4. filtrationfiltered
  5. customsolvent removed in vacuo
  6. customto give 95.8 g of crude product
  7. customThe crude product is purified by column chromatography on silica gel (500 g, hexane)

Sources & evidence

ORD record
ord-af6ac580e31c4528862973d55bd3837f
Source dataset
uspto-grants-1980_01
Patent number
US04182717

Reaction notes

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