2-Methyl-2-butene → HCID 89497979, compound

HRID 1430313Notes

Reaction equation

HRID 1430313 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:15][CH2:16][CH:17]=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]=1[CH3:7].CC(=CC)C.[O-:24]Cl=O.[Na+].[NH4+].[Cl-]>C(O)(C)(C)C.O1CCCC1.O>[Br:1][C:2]1[CH:3]=[N:4][N:5]([CH2:8][C:9]2([O:15][CH2:16][C:17]([OH:24])=[O:18])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[C:6]=1[CH3:7]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 25517Ammonium ChlorideHCID 23668197Sodium ChloriteHCID 89497975HCID 89497975, compound

Product 1

HCID 89497979HCID 89497979, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 174A (3.15 g) in t-butanol (200 mL) and tetrahydrofuran (50 mL) was added 2-methyl-2-butene (8 mL). The mixture was allowed to stir in an ice bath. NaClO2 (1.2 g) and NaH2PO4 (3 g) were dissolved into water (75 mL), and the solution was added to the mixture. The mixture was allowed to stir in an ice bath for 15 minutes, and then stirred at room temperature for 12 hours. NH4Cl was added, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and concentrated to dryness to provide the title compound.

Workup

  1. additionthe solution was added to the mixture
  2. stirringto stir in an ice bath for 15 minutes
  3. stirringstirred at room temperature for 12 hours
  4. extractionthe mixture was extracted with ethyl acetate
  5. washthe organic layer was washed with brine
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-ae7edd3cc19e46c69f7f07ff6ae733d4
Source dataset
uspto-grants-2015_01
Patent number
US08940737B2

Reaction notes

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