3,4-dihydro-2H-pyran → 2-Methyl-3-butyn-2-yl 2-tetrahydropyranyl ether

HRID 734364Notes

Reaction equation

HRID 734364 reaction equation
[CH3:1][C:2]([OH:6])([C:4]#[CH:5])[CH3:3].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1>ClCCl.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:1][C:2]([CH3:3])([O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1)[C:4]#[CH:5]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 82582-Methyl-3-butyn-2-ol

Product 1

HCID 41938432-Methyl-3-butyn-2-yl 2-tetrahydropyranyl etherYield 100%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-3-butyn-2-ol (17.0 g, 202.1 mmol) in dichloromethane (200 mL) cooled to 0° C. was added 2,3-dihydropyran (22.0 mL, 258.4 mmol), followed by para-toluenesulfonic acid (10 mg, 0.05 mmol). The mixture was allowed to slowly warm to room temperature over 3 h, then washed with a saturated aqueous solution of sodium bicarbonate, followed by brine, then dried (sodium sulfate), and concentrated to provide 34.0 g (97%) of 2-(1,1-dimethyl-prop-2-ynyloxy)-tetrahydropyran as a clear oil.

Workup

  1. washwashed with a saturated aqueous solution of sodium bicarbonate
  2. dry with materialdried (sodium sulfate)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-55ae80f2158b4540991add1349a208b9
Source dataset
uspto-grants-2009_09
Patent number
US07592353B2

Reaction notes

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