Hydrochloric Acid → HCID 46195899, compound

HRID 2360101Notes

Reaction equation

HRID 2360101 reaction equation
[CH:1]1[CH:10]=[C:9]([OH:11])[CH:8]=[C:7]2[C:2]=1[CH:3]1[O:14][C:13]3[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=3[CH:4]1[CH2:5][O:6]2.[H-].[Na+].[CH:21](I)([CH3:23])[CH3:22].Cl>CN(C=O)C.O>[CH:21]([O:11][C:9]1[CH:8]=[C:7]2[C:2]([CH:3]3[O:14][C:13]4[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=4[CH:4]3[CH2:5][O:6]2)=[CH:1][CH:10]=1)([CH3:23])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 391074HCID 391074, compound

Product 1

HCID 46195899HCID 46195899, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 6a,11a-Dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol (100 mg, 0.42 mmol) was dissolved in DMF (5 ml) and NaH (10 mg, 0.42 mmol) was added to the solution at room temperature, followed by isopropyl iodide (149 mg, 0.84 mmol). The reaction mixture was stirred at room temperature to 6 hours and poured into iced water and neutralized with 10% HCl to get the white precipitate. Precipitate were washed with water and purified by silica gel column chromatography using hexane-chloroform as the eluent to give 3-isopropoxy-6a,11a-dihydro-6H-benzofuro[3,2-c]chromene (60 mg, 51%) as white solid.

Workup

  1. customto get the white precipitate
  2. washPrecipitate were washed with water
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-79bbdb26e86a449d918d07a8353cb8ca
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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