Hydrochloric Acid → HCID 46195900, compound

HRID 2360102Notes

Reaction equation

HRID 2360102 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+].[CH2:21](Br)[CH:22]=[CH2:23].Cl>CN(C=O)C.O>[CH2:23]([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)[CH:22]=[CH2:21]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 391074HCID 391074, compound

Product 1

HCID 46195900HCID 46195900, compoundYield 50%

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 allyl bromide (0.07 ml, 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-(allyloxy)-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-52aff6be06324fac8699980702e44da9
Source dataset
uspto-grants-2014_04
Patent number
US08686028B2

Reaction notes

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