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

HRID 892861Notes

Reaction equation

HRID 892861 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>[Br:1][CH2:2][CH2:3][O:4][CH:6]1[CH2:7][CH2:8][CH2:9][CH2:10][O:5]1

Participants

4

Reactant 2

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

Product 1

HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranYield 50.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-bromoethanol (10.00 g, 80 mmol) and 3,4-dihydro-2H-pyran (10.1 g, 120 mmol) in CH2Cl2 (400 mL) was added a spatula of Amberlyst-15 ion exchange resin and the reaction was stirred for 18 hrs. It was then filtered through Celite and concentrated. Distillation (40 mm Hg, b.p.=102° C.) afforded tetrahydro-2-(2-bromoethoxy)-2H-pyran (8.49 g).

Workup

  1. filtrationIt was then filtered through Celite
  2. concentrationconcentrated
  3. distillationDistillation (40 mm Hg, b.p.=102° C.)

Sources & evidence

ORD record
ord-86644044dc4b4dbc9e71a5e7fada3574
Source dataset
uspto-grants-1992_06
Patent number
US05120752

Reaction notes

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