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

HRID 2200531Notes

Reaction equation

HRID 2200531 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].[O:6]1[CH:11]=[CH:10][CH2:9][CH2:8][CH2:7]1>C(Cl)Cl.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11][O:6]1

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 123083-Bromo-1-propanol

Product 1

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranYield 69%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 3-bromopropan-1-ol (8 g, 57.9 mmol) in DCM (100 mL) was added PPTS (891 mg, 3.6 mmol), then dihydropyran (7.3 g, 86.9 mmol) was added dropwise at 0° C. The mixture was stirred at room temperature overnight. 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-(3-bromopropoxy)tetrahydro-2H-pyran (8.9 g, 69.0% 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-af511a4ac49a442eac8a0dc16aa320de
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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