Sodium Carbonate → 8-Methoxypsoralen

HRID 59639Notes

Reaction equation

HRID 59639 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([O:16][CH3:17])[C:14]=1[OH:15])[O:11][C:10](=[O:18])[CH:9]=[CH:8]2)=O.C(=O)([O-])[O-].[Na+].[Na+].[BH4-].[Na+]>CC(C)=O.S(=O)(=O)(O)O>[CH3:17][O:16][C:13]1[C:12]2[O:11][C:10]([CH:9]=[CH:8][C:7]=2[CH:6]=[C:5]2[CH:3]=[CH:2][O:15][C:14]=12)=[O:18]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 4311764Sodium borohydrideHCID 118376979HCID 118376979, compound

Product 1

HCID 41148-MethoxypsoralenYield 80%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 1118Sulfuric AcidSolvent

Procedure

1.5 g of 6-(2′-chloroacetyl)-7-hydroxy-8-methoxycoumarin (0.006 mole) is cyclized by heating in 20 ml of acetone in the presence of 0.5 g sodium carbonate (0.007 mole), reducing using 1.4 mg of sodium borohydride (0.03 mole) and neutralizing in sulfuric acid medium. After vacuum filtration and evaporation and trituration in ethanol, 8-MOP is obtained (yield 80%). Lastly, the 8-MOP is recrystallized in ethanol.

Workup

  1. filtrationAfter vacuum filtration and evaporation and trituration in ethanol

Sources & evidence

ORD record
ord-283c87b7a0854014a44f533f237ffa58
Source dataset
uspto-grants-2016_09
Patent number
US09440940B2

Reaction notes

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