Water → HCID 21186704, compound

HRID 1384285Notes

Reaction equation

HRID 1384285 reaction equation
[CH:1]([C:3]1[CH:26]=[CH:25][C:6]([O:7][CH2:8][C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:12]3=[CH:11][C:10]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:5][CH:4]=1)=[O:2].Cl([O-])=[O:28].[Na+].O.O.P([O-])(O)(O)=O.[Na+].O>CC(O)(C)C.CC(=CC)C.C(Cl)(Cl)Cl>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][C:9]2[N:14]=[C:13]3[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:12]3=[CH:11][C:10]=2[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:25][CH:26]=1)([OH:28])=[O:2]

Participants

8

Reactant 4

HCID 962WaterHCID 21186726HCID 21186726, compoundHCID 23668197Sodium ChloriteHCID 23673460Sodium Phosphate, Monobasic, Dihydrate

Product 1

HCID 21186704HCID 21186704, compoundYield 89.1%

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolvent2×HCID 6386tert-ButanolSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

Ethyl 2-(4-formylphenoxymethyl)-6,7,8,9-tetrahydro-5H-cyclohepta[b]pyridine-3-carboxylate (3.05 g, 8.63 mmol) was dissolved in a mixed solution of 2-methyl-2-propanol (33.0 ml) and 2-methyl-2-butene (10.0 ml), and to the solution was added dropwise aqueous solution (26.0 ml) of sodium chlorite (80%, 4.88 g, 43.2 mmol) and sodium dihydrogenphosphate dihydrate (4.46 g, 28.6 mmol). Chloroform was added until insoluble matter was dissolved and then the solution was stirred at room temperature for 3.5 hours. The reaction solution was diluted with chloroform, mixed with water and then extracted with chloroform-methanol mixed solution (5:1). The thus obtained organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1) to obtain the title compound (2.84 g, 89.1%) as white powder.

Workup

  1. dissolutionwas dissolved
  2. extractionextracted with chloroform-methanol mixed solution (5:1)
  3. washThe thus obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-2f44d69173f04275bf0bab0f48e160e8
Source dataset
uspto-grants-2001_07
Patent number
US06258829B1

Reaction notes

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