2-Methyl-2-butene → HCID 86644918, compound

HRID 1875065Notes

Reaction equation

HRID 1875065 reaction equation
[O-:1]Cl=O.[Na+].[N:5]([C:8]1[N:9]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]([CH:14]=[O:15])=[C:11]([Cl:13])[N:12]=1)=[N+:6]=[N-:7].CC(=CC)C>O.C1COCC1.CC(O)(C)C>[N:5]([C:8]1[N:9]([CH2:16][O:17][CH2:18][CH2:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[C:10]([C:14]([OH:1])=[O:15])=[C:11]([Cl:13])[N:12]=1)=[N+:6]=[N-:7]

Participants

7

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 71534032HCID 71534032, compound

Product 1

HCID 86644918HCID 86644918, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of NaClO2 (21.7 g, 240 mmol) and NaH2PO4.2H2O (19.9 g, 144 mmol) in H2O (51 mL) was added to a stirred solution of 2-azido-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carbaldehyde (7.2 g, 24.0 mmol) and 2-methyl-2-butene (144 mL of a 2M solution in THF, 2887 mmol) in THF (72 mL) and t-BuOH (17 mL). The reaction mixture was stirred at RT for 1 h and extracted with EtOAc. The organic layer was dried (Na2SO4), filtered and dried to provide 2-azido-4-chloro-1-({[2-(trimethylsilyl)ethyl]oxy}methyl)-1H-imidazole-5-carboxylic acid as a clear oil that was assumed to be quantitative and used without further purification. The above acid (1.40 mmol) was stirred in a solution of TFA (2.15 mL, 27.9 mmol) in CH2Cl2 (2 mL) for 1 h at RT. Sat'd NaHCO3 was added and the mixture was washed with EtOAc. The aqueous layer was isolated, acidified with 1N HCl and extracted thoroughly with EtOAc. The organic layer was dried (Na2SO4), filtered, concentrated, and triturated with hexanes and again with diethyl ether to provide the title compound as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 13.33 (br. s., 1H), 12.77 (br. s., 1H).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-5402e77098f54a449b1f085b12b7af8b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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