Lithium Hydroxide → Porphyrin precursor

HRID 1604726

反応式

HRID 1604726 の反応式
C([O:4][CH2:5][CH2:6][CH2:7][C:8]1[C:12]([CH3:13])=[C:11]([CH:14]=[O:15])[NH:10][C:9]=1[CH2:16][C:17]1[NH:18][C:19]([CH2:26][C:27]2[NH:28][C:29]([CH:40]=[O:41])=[C:30]([CH3:39])[C:31]=2[CH2:32][CH2:33][CH2:34][O:35]C(=O)C)=[C:20]([CH2:24][CH3:25])[C:21]=1[CH2:22][CH3:23])(=O)C.[Li+].[OH-]>CO>[CH:40]([C:29]1[NH:28][C:27]([CH2:26][C:19]2[NH:18][C:17]([CH2:16][C:9]3[NH:10][C:11]([CH:14]=[O:15])=[C:12]([CH3:13])[C:8]=3[CH2:7][CH2:6][CH2:5][OH:4])=[C:21]([CH2:22][CH3:23])[C:20]=2[CH2:24][CH3:25])=[C:31]([CH2:32][CH2:33][CH2:34][OH:35])[C:30]=1[CH3:39])=[O:41]

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 543211662,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole

生成物 1

HCID 11237009Porphyrin precursor収率 94%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

7H, FIG. 7. 2,5-Bis[(3-acetoxypropyl-5-formyl-4-methylpyrrol-2-yl)methyl]-3,4-diethylpyrrole 7G (5.98 g, 0.011 mol) and LiOH (1.76 g, 0.042 mol) were added to 400 mL of 95% methanol, which had been degassed with nitrogen prior to use, and the mixture heated to reflux under a nitrogen atmosphere. The reaction became homogeneous when heated. After heating for 1.25 hours, the reaction was allowed to cool to room temperature. The product precipitated as a tan color solid as the reaction cooled. The volume of the reaction mixture was reduced to 75 mL on a rotary evaporator and the resulting slurry placed in the freezer for several hours. The product was filtered and then purified by forming a slurry with 400 mL of methanol and 50 mL of water and heating close to boiling. The slurry was first cooled to room temperature, reduced to 1/2 volume under reduced pressure, and placed in the freezer for several hours. The product was collected by filtration and vacuum dried to yield 4.96 g of a tan powder (94%): 1H NMR (CD3OD, 300 MHz): δ0.96 (6H, t, CH2CH3), 1.49 (4H, p, CH2CH2CH2OH), 2.25 (6H, s, pyrrole--CH3), 2.32-2.43 (8H, m, CH2CH3 and CH2CH2CH2OH), 3.46 (4H, t, CH2CH2CH2OH), 3.85 (4H, s, (pyrrole)2 --CH2),9.34 (2H, s, CHO); CI MS (M+) 480; HRMS (M)+, 481.2942 (calc for C28H39N3O4, 481.2941).

後処理

  1. customhad been degassed with nitrogen
  2. temperaturethe mixture heated
  3. temperatureto reflux under a nitrogen atmosphere
  4. temperatureheated
  5. temperatureAfter heating for 1.25 hours
  6. customThe product precipitated as a tan color solid as the reaction
  7. temperaturecooled
  8. customThe volume of the reaction mixture was reduced to 75 mL on a rotary evaporator
  9. waitthe resulting slurry placed in the freezer for several hours
  10. filtrationThe product was filtered
  11. custompurified
  12. customby forming a slurry with 400 mL of methanol and 50 mL of water
  13. temperatureheating
  14. customclose
  15. temperatureThe slurry was first cooled to room temperature
  16. waitplaced in the freezer for several hours
  17. filtrationThe product was collected by filtration and vacuum
  18. customdried

出典と根拠

ORDレコード
ord-28dd05be24244e7d9a07b7b3a5fde56e
出典データセット
uspto-grants-1999_11
特許番号
US05994535

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