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

HRID 1906913Notes

Reaction equation

HRID 1906913 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4][OH:5].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1.[O:23]1[CH:28]=[CH:27][CH2:26][CH2:25][CH2:24]1>ClCCl>[Br:1][CH2:2][CH2:3][CH2:4][O:5][CH:24]1[CH2:25][CH2:26][CH2:27][CH2:28][O:23]1

Participants

5

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 123083-Bromo-1-propanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyran

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-bromo-1-propanol (10 mmole) in dichloromethane (20 ml) containing pyridinium p-toluene sulfonate (150 mg) is stirred with dihydropyran (15 mmole) for 20 hours at ambient temperature. The solution is then washed with water, dried (MgSO4 anhydrous), evaporated and is chromatographed on silica gel to afford the title compound.

Workup

  1. washThe solution is then washed with water
  2. dry with materialdried (MgSO4 anhydrous)
  3. customevaporated
  4. customis chromatographed on silica gel

Sources & evidence

ORD record
ord-f214f79358cc41debdadf619fab2b425
Source dataset
uspto-grants-1987_03
Patent number
US04654364

Reaction notes

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