2-Methyl-2-butene → HCID 69813108, compound

HRID 1809464Notes

Reaction equation

HRID 1809464 reaction equation
[OH:1][CH2:2][C:3]1[C:4]2[C:8]([CH:9]=[CH:10][CH:11]=1)=[N:7][N:6]([C:12]1[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=1)[CH:5]=2.CC(=CC)C.[O-:25]Cl=O.[Na+]>C(Cl)Cl.[O-2].[Mn+4].[O-2]>[C:16]([C:15]1[CH:14]=[CH:13][C:12]([N:6]2[CH:5]=[C:4]3[C:8]([CH:9]=[CH:10][CH:11]=[C:3]3[C:2]([OH:25])=[O:1])=[N:7]2)=[CH:19][CH:18]=1)#[N:17]

Participants

6

Reactant 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 69809508HCID 69809508, compound

Product 1

HCID 69813108HCID 69813108, compound

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (C5) in dry DCM (0.07 M) was added manganese (IV) oxide. The reaction mixture was stirred at RT for 2 h. Then, the suspension was filtered and the precipitated washed several times with DCM. The combined organic extracts were concentrated to dryness. The resulting crude was dissolved in a mixture of water/tert-butanol (1:1, 0.04 M). Afterwards, 2-methyl-2-butene (20 eq., 2 M in THF), NaH2PO4 (8 eq.) and NaClO2 (8 eq.) were added. The reaction mixture was stirred at RT for 30 min. Then, the mixture was extracted with DCM (3×) and the organic extracts washed with brine (2×) and dried (Na2SO4). Evaporation of the solvent gave the title compound as a yellow powder that was used in the next step without further purification. 1H NMR (300 MHz, DMSO-d6, 300K) δ 13.23 (1H, bs), 9.38 (1H, s), 8.45 (2H, d, J=7.3 Hz), 8.12-8.09 (3H, m), 7.91 (1H, d, J=6.8 Hz), 7.52 (1H, t, J=7.0 Hz). MS (ES+) C15H9N3O2 required: 263, found: 264 (M+H)+.

Workup

  1. filtrationThen, the suspension was filtered
  2. washthe precipitated washed several times with DCM
  3. concentrationThe combined organic extracts were concentrated to dryness
  4. dissolutionThe resulting crude was dissolved in a mixture of water/tert-butanol (1:1, 0.04 M)
  5. stirringThe reaction mixture was stirred at RT for 30 min
  6. extractionThen, the mixture was extracted with DCM (3×)
  7. washthe organic extracts washed with brine (2×)
  8. dry with materialdried (Na2SO4)
  9. customEvaporation of the solvent

Sources & evidence

ORD record
ord-ff42a8b9b2644405959a4e1c870b6f4a
Source dataset
uspto-grants-2013_01
Patent number
US08362030B2

Reaction notes

Loading…