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

HRID 2200530Notes

Reaction equation

HRID 2200530 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1>C(Cl)Cl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[Br:1][CH2:2][CH2:3][O:4][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:5]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 108982-Bromoethanol

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranYield 72%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromoethanol (15 g, 0.12 mol) in DCM (150 mL) was added PPTS (891 mg, 3.6 mmol), then dihydropyran (10.6 g, 0.126 mol) was added dropwise at 0° C. The mixture was stirred at room temperature for 4 h. It was partitioned between DCM and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product which was purified by column chromatography eluting with petroleum ether/ethyl acetate (50:1) to give 2-(2-bromoethoxy)tetrahydro-2H-pyran (18.0 g, 72.0% yield) as a light yellow oil.

Workup

  1. customIt was partitioned between DCM and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product which
  7. customwas purified by column chromatography
  8. washeluting with petroleum ether/ethyl acetate (50:1)

Sources & evidence

ORD record
ord-edef336255b34ec1a569a8ad5d93309b
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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