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

HRID 6594

Reaction equation

HRID 6594 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][OH:6].[O:7]1[CH:12]=[CH:11][CH2:10][CH2:9][CH2:8]1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.P(Cl)(Cl)(Cl)=O>[Br:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][CH:8]1[CH2:9][CH2:10][CH2:11][CH2:12][O:7]1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 11430Potassium CarbonateHCID 1183884-Bromobutanol

Product 1

HCID 5590192-(4-Bromobutoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 24813Phosphorus oxychlorideSolvent

Procedure

To a solution of commercially available 4-bromobutan-1-ol (16) (1 equi.) and 3,4-dihydropyran (17) (1.5 equi.) in dichloromethane (3 mL/mmole), phosphorus oxychloride (0.01 equi.) was added at room temperature. The reaction mixture was stirred at that temperature for 24 h. Then potassium carbonate (1 equi.) was added to the reaction mixture and the reaction mixture was stirred at room temperature for 1 h, quenched with water, extracted with dichloromethane, washed with brine, dried over MgSO4, and concentrated in vacuo. Purification by chromatography on silica gel (5% EtOAc/hexanes) afforded 2-(4-bromobutoxy)-tetrahydropyran (18), as a colorless oil (88%).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 h
  2. customquenched with water
  3. extractionextracted with dichloromethane
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customPurification by chromatography on silica gel (5% EtOAc/hexanes)

Sources & evidence

ORD record
ord-897b02d40a5c415e94fa7c6fe1ac97fb
Source dataset
uspto-grants-2006_08
Patent number
US07083832B2

Linked notes

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