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

HRID 1019239Notes

Reaction equation

HRID 1019239 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.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH:7]1[O:5][CH2:4][CH2:3][CH2:2][Br:1]

Participants

5

Reactant 2

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

Product 1

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranYield 96%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5.8 g (42 mmol) of 3-bromopropanol prepared in step B and 3.5 g (42 mmol) of dihydropyran in 15 mL of methylene chloride is added 20 mg (0.116 mmol) of p-toluenesulfonic acid, and the reaction mixture is stirred at room temperature for 7 hours, then washed with 10% NaOH solution and brine, dried, and evaporated to dryness to give 8.7 g of title product in 96% yield.

Workup

  1. washwashed with 10% NaOH solution and brine
  2. customdried
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-55dbd742ef9946b4a4c882609ed12743
Source dataset
uspto-grants-2002_11
Patent number
US06486201B1

Reaction notes

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