3,4-dihydro-2H-pyran → Tetrahydropyranyl ether

HRID 986433Notes

Reaction equation

HRID 986433 reaction equation
BrC1C=[CH:6][C:5](/[CH:8]=[C:9](\C)/[CH2:10][O:11][CH2:12][CH2:13]O)=CC=1.[O:16]1C=C[CH2:19][CH2:18][CH2:17]1.O.C1(C)C=CC(S(O)(=O)=[O:30])=CC=1.C(=O)([O-])O.[Na+]>C(Cl)Cl>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:13][CH:12]1[O:11][CH:10]1[CH2:9][CH2:8][CH2:5][CH2:6][O:30]1

Participants

6

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 20148641HCID 20148641, compound2×

Product 1

HCID 263182Tetrahydropyranyl etherYield 93%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

In 20 ml of methylene chloride were dissolved 2.13 g of 2-[(E)-3-(4-bromophenyl)-2-methylallyloxy]ethanol and 1.43 ml of 3,4-dihydro-2H-pyran and 20 mg of p-toluenesulfonic acid monohydrate was added to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction at room temperature for 3 hours. Subsequently, 30 ml of methylene chloride and 20 ml of a saturated aqueous sodium hydrogen-carbonate solution were added to the reaction mixture, and the organic layer was separated, washed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution, and then dried over anhydrous magnesium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (20:1 by volume)] to obtain 2.6 g (yield 93%) of oily tetrahydropyranyl ether of 2-[(E)-3-(4-bromophenyl)-2-methylallyloxy]ethanol.

Workup

  1. additionwas added to the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction at room temperature for 3 hours
  4. customthe organic layer was separated
  5. washwashed successively with 20 ml of water and 20 ml of a saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customafter which the solvent was removed by distillation under reduced pressure
  8. customThe residue thus obtained
  9. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (20:1 by volume)]

Sources & evidence

ORD record
ord-f726c8f0b47c4c55ac1012c1cc49235a
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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