Sulfuric Acid → HCID 69930188, compound

HRID 1839352Notes

Reaction equation

HRID 1839352 reaction equation
[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:15])([CH3:14])[CH:11]3[O:16][CH:10]3[C:9]=2[CH:17]=1)(=[O:3])[CH3:2].[CH:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25]O)=[CH:20][CH:19]=1.S(=O)(=O)(O)[OH:28].C(OCC)(=O)C>C(#N)C>[C:1]([NH:4][C:5]1[CH:6]=[CH:7][C:8]2[O:13][C:12]([CH3:14])([CH3:15])[C@@H:11]([OH:28])[C@H:10]([O:16][CH2:25][CH2:24][C:21]3[CH:22]=[CH:23][CH:18]=[CH:19][CH:20]=3)[C:9]=2[CH:17]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 60542-PhenylethanolHCID 8857Ethyl AcetateHCID 13222928HCID 13222928, compound

Product 1

HCID 69930188HCID 69930188, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 6-acetylamino-3,4-epoxy-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran (0.50 g, 2.1 mmol) and 2-phenethyl alcohol (0.50 mL, 4.2 mol) in acetonitrile (2.5 mL), a catalytic amount of concentrated sulfuric acid was added at the room temperature and stirred at the room temperature for 5 hours. Thereto, ethyl acetate was added, and the formed organic phase was washed with water, an aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate. After the solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform: ethyl acetate=1:1), the obtained pink amorphous substance was recrystallized from hexane-ethyl acetate, to obtain the intended substance as pink crystals (yield; 40%).

Workup

  1. washthe formed organic phase was washed with water
  2. dry with materialan aqueous saturated sodium hydrogencarbonate solution and an aqueous saturated sodium chloride solution, and dried over anhydrous sodium sulfate
  3. distillationAfter the solvent was distilled off
  4. customthe residue was purified by silica gel column chromatography (chloroform: ethyl acetate=1:1)
  5. customthe obtained pink amorphous substance was recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0f68958cb61644159641eb22fe739089
Source dataset
uspto-grants-2004_01
Patent number
US06677371B1

Reaction notes

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