2-Methyl-2-butene → HCID 178441713, compound

HRID 1874879Notes

Reaction equation

HRID 1874879 reaction equation
Cl([O-])=O.[Na+].[OH2:5].P([O-])(O)(O)=O.[Na+].[Cl:12][C:13]1[N:14]=[C:15]([CH2:20][CH2:21][CH2:22][CH3:23])[NH:16][C:17]=1[CH:18]=[O:19].CC(=CC)C>O.C1COCC1.C(O)(C)(C)C>[CH2:20]([C:15]1[NH:16][C:17]([C:18]([OH:5])=[O:19])=[C:13]([Cl:12])[N:14]=1)[CH2:21][CH2:22][CH3:23]

Participants

8

Reactant 4

HCID 105532-Methyl-2-buteneHCID 516949Sodium Phosphate, Monobasic, MonohydrateHCID 23668197Sodium ChloriteHCID 178418251HCID 178418251, compound

Product 1

HCID 178441713HCID 178441713, compoundYield 96.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of sodium chlorite (2.0 g, 21.6 mmol) and sodium dihydrogen phosphate monohydrate (1.8 g, 12.9 mmol) in water (4.8 mL) was added to a stirred solution of 4-chloro-2-butyl-1H-imidazole-5-carbaldehyde (0.400 g, 2.1 mmol), 2-methyl-2-butene (13.4 mL of a 2M solution in THF, 26.8 mmol), and tert-butanol (1.6 mL) in THF (6.7 mL). The reaction mixture was stirred at RT for 12 h. The aqueous phase was separated and extracted with EtOAc (4×40 mL). The combined extracts were dried (Na2SO4), filtered, concentrated and the residue was triturated with diethyl ether to provide the title compound (0.411 g, 95%) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.99 (br. s., 1H), 12.88, (br. s., 1H), 2.58 (t, 2H), 1.59 (quint, 2 H), 1.20-1.31 (sex, 2H), 0.87 (t, 3H). ES-LCMS: m/z 203.1 (M+H).

Workup

  1. customThe aqueous phase was separated
  2. extractionextracted with EtOAc (4×40 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-03b4e01785e04d6f83c12436717f54e1
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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