3,4-dihydro-2H-pyran → HCID 14523530, compound

HRID 1650636Notes

Reaction equation

HRID 1650636 reaction equation
[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[CH:5][CH:4]=1.[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCl.O1CCCC1>[Br:1][CH2:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([O:9][CH:13]2[CH2:14][CH2:15][CH2:16][CH2:17][O:12]2)=[O:8])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 225994-(Bromomethyl)benzoic acidHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)

Product 1

HCID 14523530HCID 14523530, compoundYield 54.6%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

In a mixed solvent of dichloromethane and tetrahydrofuran was dissolved 5 g of p-bromomethylbenzoic acid, and 10 g of dihydropyran and 585 mg of pyridinium p-toluenesulfonate were added to the solution and the mixture was stirred at room temperature for 6 hours. The thus-obtained solution was washed with a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of sodium chloride, dried on anhydrous magnesium sulfate and concentrated. The concentrate was recrystallized from a mixed solvent of n-hexane, ethyl acetate and chloroform to obtain 3.8 g of tetrahydropyranyl p-bromomethylbenzoate.

Workup

  1. additionwere added to the solution
  2. washThe thus-obtained solution was washed with a saturated aqueous solution of NaHCO3
  3. dry with materiala saturated aqueous solution of sodium chloride, dried on anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe concentrate was recrystallized from a mixed solvent of n-hexane, ethyl acetate and chloroform

Sources & evidence

ORD record
ord-58998a1650764f2991f4e156262d487c
Source dataset
uspto-grants-1990_05
Patent number
US04925591

Reaction notes

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