Sulfuric Acid → HCID 19041752, compound

HRID 1684054Notes

Reaction equation

HRID 1684054 reaction equation
[CH3:1][C@H:2]1[C@@:7]23[C:13]([O:14][C@H:5]([CH2:6]2)[CH2:4][C@@H:3]1[C:17]1[CH:18]=[CH:19][C:20]2[O:25][CH2:24][O:23][C:21]=2[CH:22]=1)=[CH:12][C:10](=[O:11])[C:9]([O:15]C)=[CH:8]3.S(=O)(=O)(O)O>O>[O:25]1[C:20]2[CH:19]=[CH:18][C:17]([CH:3]3[CH:2]([CH3:1])[C:7]45[CH2:6][CH:5]([O:14][C:13]4=[CH:12][C:10](=[O:11])[C:9]([OH:15])=[CH:8]5)[CH2:4]3)=[CH:22][C:21]=2[O:23][CH2:24]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 9819306(2S,4S,5R,5aS)-4-(1,3-Benzodioxol-5-yl)-2,3,4,5-tetrahydro-7-methoxy-5-methyl-8H-2,5a-methano-1-benzoxepin-8-one

Product 1

HCID 19041752HCID 19041752, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Futoenone (50 mg, 0.15 mmol) and 30% sulfuric acid (7.5 ml) are added to a 25 ml round bottom flask. This mixture is heated with a heating mantle to reflux for approximately six hours. The reaction mixture is diluted with distilled water and crystals begin to precipitate. The flask is placed in a refrigerator to aid in precipitation. The crystals are collected by filtration, 300 mg (80%). M+(CI)=327. 1H NMR ppm: 0.59 (3H, d), 1.25 (1H, s), 1.72 (1H, t), 2.03 (1H, m), 2.17 (1h, d), 2.35 (2H, m), 2.53 (1H, m), 5.06 (1H, t), 5.72 (1H, s), 5.83 (1H, s), 5.93 (2H, s), 6.69 (3H, m).

Workup

  1. temperatureThis mixture is heated with a heating mantle
  2. temperatureto reflux for approximately six hours
  3. customto precipitate
  4. customThe flask is placed in a refrigerator to aid in precipitation
  5. filtrationThe crystals are collected by filtration, 300 mg (80%)

Sources & evidence

ORD record
ord-d01a6c7ed80c4b4a95775199496d5e8f
Source dataset
uspto-grants-1997_06
Patent number
US05639782

Reaction notes

Loading…