p-Toluenesulfonic acid → 2-(2-Bromoethoxy)tetrahydro-2H-pyran

HRID 1797882Notes

Reaction equation

HRID 1797882 reaction equation
[Br:1][CH2:2][CH2:3][OH:4].[O:5]1[CH:10]=[CH:9][CH2:8][CH2:7][CH2:6]1.CC1C=CC(S(O)(=O)=O)=CC=1>C(Cl)Cl.O>[Br:1][CH2:2][CH2:3][O:4][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:5]1

Participants

6

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 108982-Bromoethanol

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranYield 896.8%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-bromoethanol 24 (50.0 g, 40 mmol) in methylene chloride (500 mL) cooled to 0° C. was added 3,4-dihydro-2H-pyran (40.32 g, 48 mmol) followed by p-TSA.H2O (100 mg) was added. Reaction mixture was stirred at 0° C. for 5.0 h. The reaction mixture was washed with aq NaHCO3 and brine, dried over Na2SO4 and evaporated to give the product 25 (75.0 g, 90%). This crude product was taken to next step without purification.

Workup

  1. customReaction mixture
  2. washThe reaction mixture was washed with aq NaHCO3 and brine
  3. dry with materialdried over Na2SO4
  4. customevaporated

Sources & evidence

ORD record
ord-01cb2e7f22014058bf5764138336434d
Source dataset
uspto-grants-2013_01
Patent number
US08343950B2

Reaction notes

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