2-Methyl-2-butene → HCID 178432882, compound

HRID 1874865Notes

Reaction equation

HRID 1874865 reaction equation
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[Cl:12][C:13]1[N:14]=[C:15]([CH3:20])[NH:16][C:17]=1[CH:18]=[O:19].CC(=CC)C>O.C1COCC1.C(O)(C)(C)C>[Cl:12][C:13]1[N:14]=[C:15]([CH3:20])[NH:16][C:17]=1[C:18]([OH:5])=[O:19]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 178432881HCID 178432881, compound

Product 1

HCID 178432882HCID 178432882, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium chlorite (1.4 g, 15.3 mmol) and sodium dihydrogen phosphate monohydrate (1.2 g, 8.7 mmol) in water (3.3 mL) was added to a stirred solution of 4-chloro-2-methyl-1H-imidazole-5-carbaldehyde (0.308 g, 2.1 mmol), 2-methyl-2-butene (9.3 mL of a 2M solution in THF, 18.6 mmol), and tert-butanol (1.2 mL) in THF (4.7 mL). The reaction mixture was stirred at RT for 6 h. The aqueous phase was separated and extracted with EtOAc (4×10 mL). The combined extracts were dried (Na2SO4), filtered, concentrated and the residue was triturated with diethyl ether to provide the title compound (0.168 g, 50%) as white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.98 (br. s., 1H), 12.88, (br. s., 1H), 2.26 (s, 3H). ES-LCMS: m/z 160.9 (M+1).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with EtOAc (4×10 mL)
  3. dry with materialThe combined extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was triturated with diethyl ether

Sources & evidence

ORD record
ord-316f1aed55094209bc9e0a945bf5baaa
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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