3,4-dihydro-2H-pyran → 2-(3-Butynyloxy)tetrahydro-2H-pyran

HRID 870558Notes

Reaction equation

HRID 870558 reaction equation
[CH2:1]([OH:5])[CH2:2][C:3]#[CH:4].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+]>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1)[CH2:2][C:3]#[CH:4]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 135663-Butyn-1-OLHCID 516892Sodium Bicarbonate

Product 1

HCID 1424402-(3-Butynyloxy)tetrahydro-2H-pyranYield 82%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-butyn-1-ol (50 g, 1 equiv, 713 mmol), p-toluenesulfonic acid monohydrate (1.36 g, 0.01 equiv, 7.13 mmol), and dihydropyran (71.7 mL, 1.10 equiv, 785 mmol) in dichloromethane (500 mL) is stirred at 25° C. for 24 hours. Saturated sodium bicarbonate solution (500 mL) is then slowly added, and the mixture is extracted with dichloromethane (500 mL). The organic extract is dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude product, which is purified by vacuum distillation to afford the title compound (90 g, 82%): b.p.: 65° C., 1 mm Hg.

Workup

  1. extractionthe mixture is extracted with dichloromethane (500 mL)
  2. extractionThe organic extract
  3. dry with materialis dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto afford the crude product, which
  7. distillationis purified by vacuum distillation

Sources & evidence

ORD record
ord-9ce5ff160b5840c2b2d34bd0564c7b82
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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