Hydrochloric Acid → HCID 46195899, compound

HRID 2360098Notes

Reaction equation

HRID 2360098 reaction equation
C[C:2]1[C:3]([OH:19])=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH:8]1[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[O:14][CH:7]21.[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24].Cl>CN(C=O)C.O>[CH:23]([O:19][C:3]1[CH:2]=[C:11]2[C:6]([CH:7]3[O:14][C:13]4[CH:15]=[CH:16][CH:17]=[CH:18][C:12]=4[CH:8]3[CH2:9][O:10]2)=[CH:5][CH:4]=1)([CH3:24])[CH3:22]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 46195897HCID 46195897, compound

Product 1

HCID 46195899HCID 46195899, compoundYield 60.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Compound 4-methyl-6a,11a-dihydro-6H-benzo[4,5]furo[3,2-c]chromen-3-ol (100 mg, 0.34 mmol) was dissolved in DMF (5 ml) and NaH (8.1 mg, 0.34 mmol) was added to the solution at room temperature, followed by allyl bromide (0.06 ml, 0.68 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 (58 mg, 50%) 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-c7f8806b640e4c93a3ffbc55a5e0abb7
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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