Methanol → HCID 14985932, compound

HRID 1654808Notes

Reaction equation

HRID 1654808 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:10]2[C:11](=[O:16])[CH:12]=[C:13]([CH3:15])[O:14][C:9]=2[C:8]([O:17][CH3:18])=[C:7]([OH:19])[C:6]=1[C:20]([O:22][CH3:23])=[O:21].I[CH3:25].CO>CN(C)C=O.C(OCC)C.O>[CH3:15][C:13]1[O:14][C:9]2[C:8]([O:17][CH3:18])=[C:7]([O:19][CH3:25])[C:6]([C:20]([O:22][CH3:23])=[O:21])=[C:5]([O:4][CH3:3])[C:10]=2[C:11](=[O:16])[CH:12]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydride2×HCID 14985931HCID 14985931, compound

Product 1

HCID 14985932HCID 14985932, compoundYield 76.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

With protection from moisture, 0.42 g (10.6 mmol) of sodium hydride (60% dispersion) is slowly added at 60° C., with stirring, to 3.10 g (10.6 mmol) of methyl 5,8-dimethoxy-7-hydroxy-2-methyl-4-oxo-4H-1-benzopyran-6-carboxylate dissolved in 50 ml of anhydrous dimethylformamide. After a contact period of 11/2 hours, 1.30 ml (21.2 mmol) of iodomethane are added to the reaction mixture and stirring is continued for 2 hours. After decomposition of the excess sodium hydride by the addition of methanol, the reaction mixture, diluted with diethyl ether, is filtered. Evaporation of the filtrate results in an orange oil which is taken up in water and extracted 3 times with 50 ml of diethyl ether each time. The combined organic phases are washed with a saturated solution of NaCl and dried over Na2SO4 and then the solvents are removed. Chromatography of the powdery residue on a silica gel column (70-230 mesh; eluant: CH2Cl2 /CH 3 OH: 99/1) yields 2.5 g of orange crystals.

Workup

  1. filtrationis filtered
  2. customEvaporation of the filtrate
  3. customresults in an orange oil which
  4. extractionextracted 3 times with 50 ml of diethyl ether each time
  5. washThe combined organic phases are washed with a saturated solution of NaCl
  6. dry with materialdried over Na2SO4
  7. customthe solvents are removed

Sources & evidence

ORD record
ord-904fb22624cf4716b5cdb095ce031fd8
Source dataset
uspto-grants-1995_04
Patent number
US05409952

Reaction notes

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