2-Methyl-2-butene → HCID 178440111, compound

HRID 1874857Notes

Reaction equation

HRID 1874857 reaction equation
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[Cl:12][C:13]1[N:14]=[C:15]([CH:20]([CH3:22])[CH3:21])[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]([CH:20]([CH3:22])[CH3:21])[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 178440108HCID 178440108, compound

Product 1

HCID 178440111HCID 178440111, compoundYield 92%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium chlorite (0.92 g, 10.2 mmol) and sodium dihydrogen phosphate monohydrate (0.81 g, 5.9 mmol) in water (2.2 mL) was added to a stirred solution of 4-chloro-2-(1-methylethyl)-1H-imidazole-5-carbaldehyde (0.165 g, 1.0 mmol), 2-methyl-2-butene (6.2 mL of a 2M solution in THF, 12.4 mmol), and tert-butanol (0.8 mL) in THF (3.1 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 (0.173 g, 92%) as light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 12.82 (br. s., 1H), 2.95 (sept, 1H), 1.20 (d, 6H). ES-LCMS: m/z 189.0 (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-8fd7c43d958d4e05997388154c554816
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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