Ethoxyquin → 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline

HRID 1995055

Reaction equation

HRID 1995055 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[C:8]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])([CH3:14])[NH:13][C:7]2=[CH:6][CH:5]=1.[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[C@@H:24]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:23][C@@H:22]1Br)(=[O:19])[CH3:18]>CC(C)=O>[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[C@@H:24]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:23][CH:22]1[N:13]1[C:7]2[C:8](=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=2)[C:10]([CH3:16])=[CH:11][C:12]1([CH3:15])[CH3:14])(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 3293EthoxyquinHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

Product 1

HCID 131953191-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinolineYield 74.6%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethoxyquin (240 g) and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (228 g) were stirred at 80° for 18 hours. Acetone (200 ml) was added to the hot reaction mixture and stirring continued for an additional 20 minutes. After cooling, the solid ethoxyquin hydrobromide was filtered off, washed thoroughly with acetone and the combined acetone filtrates were evaporated under reduced pressure. The resulted crude product was recrystallised (iso-propanol) to yield 226.5 g of 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline. m.p.: 180°-181°.

Workup

  1. temperatureAfter cooling
  2. filtrationthe solid ethoxyquin hydrobromide was filtered off
  3. washwashed thoroughly with acetone
  4. customthe combined acetone filtrates were evaporated under reduced pressure
  5. customThe resulted crude product
  6. customwas recrystallised (iso-propanol)

Sources & evidence

ORD record
ord-2dd5c332b340495ba622b6c4fb8309e5
Source dataset
uspto-grants-1983_09
Patent number
US04402945

Linked notes

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