Acetic Acid → HCID 22419416, compound

HRID 1719992Notes

Reaction equation

HRID 1719992 reaction equation
Br.[CH2:2]([O:9][CH2:10][CH:11]1[O:16][C:15](=[O:17])[CH:14]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[N+:26]([O-:28])=[O:27])[C:13](=[O:30])[CH2:12]1)[C:3]1C=CC=CC=1.C(O)(=[O:33])C>>[C:2]([O:9][CH2:10][CH:11]1[O:16][C:15](=[O:17])[CH:14]([C:18](=[O:29])[C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=2[N+:26]([O-:28])=[O:27])[C:13](=[O:30])[CH2:12]1)(=[O:33])[CH3:3]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 22419415HCID 22419415, compound

Product 1

HCID 22419416HCID 22419416, compound

Procedure

To 7.7 ml of 25% acetic acid solution of hydrobromic acid was dissolved 2.40 g (5.7 mmole) of 6-benzyloxymethyl-3-(4-chloro-2-nitrobenzoyl)tetrahydropyran-2,4-dione, then this solution was reacted at room temperature for 5 hours. After the completion of the reaction, the mixture was poured into ice water, then extracted with chloroform. The organic solvent layer extracted was washed with water and saturated brine in turn, dried with magnesium sulfate, then the solvent was distilled therefrom. The residue obtained was purified by silica gel column chromatography to obtain 1.50 g of the objective product in a state of orange-coloured sticky oil.

Workup

  1. customthis solution was reacted at room temperature for 5 hours
  2. customAfter the completion of the reaction
  3. extractionextracted with chloroform
  4. extractionThe organic solvent layer extracted
  5. washwas washed with water and saturated brine in turn
  6. dry with materialdried with magnesium sulfate
  7. distillationthe solvent was distilled
  8. customThe residue obtained
  9. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-28698e9dc35c414ebb335b5a1abcae21
Source dataset
uspto-grants-1996_04
Patent number
US05504056

Reaction notes

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