Epichlorohydrin → HCID 19788278, compound

HRID 1656614Notes

Reaction equation

HRID 1656614 reaction equation
[OH:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9].[OH-].[Na+].[CH2:12]([CH:14]1[O:16][CH2:15]1)Cl>O>[O:16]1[CH2:15][CH:14]1[CH2:12][O:1][C:2]1[C:7](=[O:8])[CH:6]=[CH:5][O:4][C:3]=1[CH3:9]

Participants

5

Reactant 3

HCID 7835EpichlorohydrinHCID 8369MaltolHCID 14798Sodium Hydroxide

Product 1

HCID 19788278HCID 19788278, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-hydroxy-2-methyl-4-oxopyrane (12.6 g), sodium hydroxide (4 g), epichlorohydrin (9.25 g) and water (50 ml) is stirred at room temperature, under nitrogen atmosphere, for 3 hours; then it is extracted four times with chloroform (120 ml) and the organic extracts are combined, washed with water, dried and evaporated to dryness yielding 8.3 g of 3-(2,3-epoxypropoxy)-2-methyl-4-oxopyrane. A mixture of said product and 2-aminotetralin (7.3 g) in absolute ethanol (100 ml) is charged into a sealed vessel, heated to 80° C. for 5 hours, then cooled and evaporated under reduced pressure. The obtained residue is dissolved into ethyl acetate and a solution of fumaric acid in ethyl acetate is then added thereto. The precipitate which forms is recovered by filtration and crystallized from ethanol affording N-(1,2,3,4-tetrahydronaphth-2-yl)-2-hydroxy-3-(2-methyl-4-oxopyran-3-yloxy)propanamine hydrogenfumarate ((i): R=H, Ar=radical 10 wherein Z is methyl, and the chain is attached to position 2 of the tetralin moiety).

Workup

  1. extractionthen it is extracted four times with chloroform (120 ml)
  2. washwashed with water
  3. customdried
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1934d174ff91469396a2da1dc23b684e
Source dataset
uspto-grants-1993_10
Patent number
US05254595

Reaction notes

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