2-Methyl-2-butene → HCID 67474066, compound

HRID 2387734Notes

Reaction equation

HRID 2387734 reaction equation
CC(=CC)C.P([O-])(O)(O)=O.[Na+].[CH3:12][C:13]1[N:18]=[C:17]([CH3:19])[C:16]([O:20][CH2:21][C@@:22]2([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[C:29]([F:37])[CH:28]=3)[CH2:24][C@H:23]2[CH:25]=[O:26])=[CH:15][N:14]=1.Cl([O-])=[O:39].[Na+]>O.CC(C)=O.O>[CH3:12][C:13]1[N:18]=[C:17]([CH3:19])[C:16]([O:20][CH2:21][C@@:22]2([C:27]3[CH:32]=[CH:31][C:30]([O:33][CH2:34][O:35][CH3:36])=[C:29]([F:37])[CH:28]=3)[CH2:24][C@H:23]2[C:25]([OH:39])=[O:26])=[CH:15][N:14]=1

Participants

7

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 86664268HCID 86664268, compound

Product 1

HCID 67474066HCID 67474066, compoundYield 56.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

2-methyl-2-butene (11.5 ml) and sodium dihydrogen phosphate (3.89 g) were added to an acetone-water (100 ml-25 ml) solution of the compound 321-7 (7.8 g). The reaction solution was cooled on ice. Sodium chlorite (3.91 g) was added to the reaction solution, and the obtained mixture was stirred at room temperature for 15 hours. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to 0:1), so as to obtain the title compound (4.57 g).

Workup

  1. temperatureThe reaction solution was cooled on ice
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe obtained organic layer was dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (n-heptane:ethyl acetate=9:1 to 0:1)

Sources & evidence

ORD record
ord-5255d6ad5fbb4d0aa71bba0c87b50a36
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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