3,4-dihydro-2H-pyran → 2-Propanone, 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

HRID 619211Notes

Reaction equation

HRID 619211 reaction equation
O[C:2]1([CH2:11][OH:12])[CH2:7][O:6][C:5]([OH:10])([CH2:8]O)C[O:3]1.O1[CH2:18][CH2:17][O:16][CH2:15][CH2:14]1.O1C=C[CH2:22][CH2:21][CH2:20]1.[C:25](=O)(O)[O-].[Na+]>C(Cl)Cl.C(N(CC)CC)C>[O:16]1[CH2:17][CH2:18][CH2:25][CH2:14][CH:15]1[O:12][CH2:11][C:2](=[O:3])[CH2:7][O:6][CH:5]1[CH2:8][CH2:22][CH2:21][CH2:20][O:10]1

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 312751,4-DioxaneHCID 516892Sodium BicarbonateHCID 4180364Dihydroxyacetone dimer

Product 1

HCID 110106602-Propanone, 1,3-bis[(tetrahydro-2H-pyran-2-yl)oxy]-

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

9 g of 2,5-dihydroxy-1,4-dioxane-2,5-dimethanol were introduced into 60 ml of dioxane and the suspension was taken to about 70° C. for 15 minutes, then taken to ambient temperature. Then, 20 ml of 3,4-dihydro-2H-pyran and 300 mg of monohydrated p-toluene sulfonic acid were added. The temperature was held at about 40° C. and then the reaction medium stood overnight at ambient temperature. It was then poured into a mixture of 300 ml of a saturated solution of sodium bicarbonate +10 ml of triethylamine and extraction was carried out 4 times with methylene chloride. The organic phase was washed with salt water and dried. After purification by passing through silica with ethyl cycloacetate/triethylamine: 8/2 as eluant, 17 g of the expected product (pale yellow syrup) were obtained.

Workup

  1. customtaken to ambient temperature
  2. customwas held at about 40° C.
  3. waitthe reaction medium stood overnight at ambient temperature
  4. washThe organic phase was washed with salt water
  5. customdried
  6. customAfter purification

Sources & evidence

ORD record
ord-5ac8e3a25464461abce1d6f84dbe59d5
Source dataset
uspto-grants-1999_09
Patent number
US05958936

Reaction notes

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