Methanol → Porphyrinogen

HRID 1824488Notes

Reaction equation

HRID 1824488 reaction equation
CC1(C)[C:30]2[NH:31][C:27](=[C:28](F)[C:29]=2F)[C:26](C)(C)[C:24]2[NH:25][C:21](=[C:22](F)[C:23]=2F)[C:20](C)(C)[C:18]2[NH:19][C:15](=[C:16](F)[C:17]=2F)[C:14](C)(C)[C:12]2[NH:13][C:9](=[C:10](F)[C:11]=2F)[C:8](C)(C)C2NC1=C(F)C=2F.CO.FC1C=CNC=1F.CS(O)(=O)=O>CC(C)=O>[CH2:26]1[C:27]2[NH:31][C:30](=[CH:29][CH:28]=2)[CH2:8][C:9]2[NH:13][C:12](=[CH:11][CH:10]=2)[CH2:14][C:15]2[NH:19][C:18](=[CH:17][CH:16]=2)[CH2:20][C:21]2[NH:25][C:24]1=[CH:23][CH:22]=2

Participants

6

Reactant 4

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 5256196HCID 5256196, compoundHCID 54377550HCID 54377550, compound

Product 1

HCID 9548659PorphyrinogenYield 52%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

β-Decafluoro-meso-decamethylcalix[5]pyrrole, 46 and β-hexadecafluoro-meso-hexadecamethylcalix[8]pyrrole, 48. To a round bottom flask containing methanol (37.5 mL), difluoropyrrole (773 mg, 7.50 mmol), and acetone (548 μL, 7.50 mmol were added. After dissolution of the reactants, methanesulfonic acid (490 μL, 7.50 mmol) was added and the reaction mixture was allowed to stir at ambient temperature for 2 days. The reaction mixture was then washed with aqueous NaCO3 (200 mL saturated) and taken into dichloromethane (100 mL). The resulting organic layer was then washed with water (2×100 mL), dried (Na2SO4), and the solvent was removed on the rotary evaporator. Purification of the crude reaction mixture, which was found to contain 44, 46 and 48 in appriciable yields as judged by TLC analysis, was effected via flash chromatography, using hexanes-acetone 4/1 v/v as the eluent. This resulted in the isolation of 44 (rf=0.4, 560 mg, 0.98 mmol, 52%), 46 (rf=0.2, 249 mg, 0.35 mmol, 23%), and 48 (rf=0.1, 150 mg, 0.13 mmol, 14%).

Workup

  1. additionwere added
  2. additionwas added
  3. washThe reaction mixture was then washed with aqueous NaCO3 (200 mL saturated)
  4. washThe resulting organic layer was then washed with water (2×100 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed on the rotary evaporator
  7. customPurification of the crude
  8. customreaction mixture, which
  9. customin appriciable yields

Sources & evidence

ORD record
ord-bf95927159ff4187b6fd8020d8d97e54
Source dataset
uspto-grants-2006_05
Patent number
US07041819B2

Reaction notes

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