2-Methyl-2-butene → HCID 67474068, compound

HRID 2387751Notes

Reaction equation

HRID 2387751 reaction equation
CC(=CC)C.P([O-])(O)(O)=O.[Na+].Cl([O-])=[O:13].[Na+].[F:16][C:17]1[CH:18]=[C:19]([C@:23]2([CH2:28][O:29][C:30]3[C:35](=[O:36])[N:34]([CH2:37][O:38][CH3:39])[C:33]([CH3:40])=[N:32][C:31]=3[CH3:41])[CH2:25][C@H:24]2[CH:26]=[O:27])[CH:20]=[CH:21][CH:22]=1>C(Cl)(Cl)Cl.O.CC(C)=O.O>[F:16][C:17]1[CH:18]=[C:19]([C@:23]2([CH2:28][O:29][C:30]3[C:35](=[O:36])[N:34]([CH2:37][O:38][CH3:39])[C:33]([CH3:40])=[N:32][C:31]=3[CH3:41])[CH2:25][C@H:24]2[C:26]([OH:13])=[O:27])[CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 87337461HCID 87337461, compound

Product 1

HCID 67474068HCID 67474068, compoundYield 100.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

2-methyl 2-butene (1.14 ml), sodium dihydrogen phosphate (389 mg) and sodium chlorite (305 mg) were added to an acetone-water mixed solvent (8 ml-2 ml) of the compound 326-8 (779 mg). The obtained mixture was stirred at room temperature for 1 hour. Thereafter, water was added to the reaction solution, and chloroform was added to the reaction solution to carry out liquid separation and extraction. A small amount of 1 N hydrochloric acid was added to the obtained extract, and chloroform was further added to the reaction solution to carry out liquid separation and extraction. The obtained organic layer was dried over magnesium sulfate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure, so as to obtain a crude product of the title carboxylic acid (814 mg).

Workup

  1. additionwas added to the reaction solution
  2. customliquid separation and extraction
  3. additionA small amount of 1 N hydrochloric acid was added to the obtained
  4. extractionextract
  5. additionchloroform was further added to the reaction solution
  6. customliquid separation and extraction
  7. dry with materialThe obtained organic layer was dried over magnesium sulfate
  8. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-19b186198e2a453a97bcd384826e235e
Source dataset
uspto-grants-2012_09
Patent number
US08268848B2

Reaction notes

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