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

HRID 379440Notes

Reaction equation

HRID 379440 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.C(OCC)C>[O:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH:6]1[O:4][CH2:3][CH2:2][Br:1]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 108982-BromoethanolHCID 22033616Pyridinium.p-toluenesulfonate

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Combine 2-bromoethanol (14.2 mL, 200 mmol) and dihydropyrane (18.25 mL, 200 mmol) in dichloromethane (20 mL). Add Pyridinium p-toluenesulfonic acid (5 g, 20 mmol). After 2.5 hours, dilute the reaction mixture with diethyl ether and extract with water, 1/1 water/brine, water, and then brine. Dry the organic layer over MgSO4, filter, and evaporate in vacuo to give a residue. Distill the residue to give the title compound: bp; 80-90° C. at 15-20 mm Hg.

Workup

  1. extractionextract with water, 1/1 water/brine, water
  2. dry with materialDry the organic layer over MgSO4
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue
  6. distillationDistill the residue

Sources & evidence

ORD record
ord-02442c88ffa44102b4f75b10bbf3aab8
Source dataset
uspto-grants-2001_10
Patent number
US06297259B1

Reaction notes

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