Methanol → HCID 57912400, compound

HRID 418837Notes

Reaction equation

HRID 418837 reaction equation
Br[CH2:2][C:3]1[C:12](=[O:13])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[O:5][C:4]=1[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1.[CH3:21][O-:22].[Na+].CO>CC(O)=O>[OH:20][C:17]1[CH:18]=[CH:19][C:14]([C:4]2[O:5][C:6]3[C:11]([C:12](=[O:13])[C:3]=2[CH2:2][O:22][CH3:21])=[CH:10][CH:9]=[CH:8][CH:7]=3)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 66650305HCID 66650305, compound

Product 1

HCID 57912400HCID 57912400, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3-bromomethyl-2-(4-hydroxyphenyl)-4H-chromen-4-one (0.52 g, 1.57 mmol), sodium methoxide (1.36 mL, 6.28 mmol, 25% in MeOH) and anhydrous MeOH (10 mL) was stirred overnight at rt. The reaction mixture was neutralized by addition of AcOH and the solvent was removed. The residue was poured into water and the solid was collected and purified by column chromatography (hexane:EtOAc 2:1) to give 155 mg of 2-(4-hydroxyphenyl)-3-(methoxymethyl)-4H-chromen-4-one (35.0%). MS (ES) m/z: 283.95 (M+1), 282.93 (M); Mp. 237-239° C.

Workup

  1. customthe solvent was removed
  2. additionThe residue was poured into water
  3. customthe solid was collected
  4. custompurified by column chromatography (hexane:EtOAc 2:1)

Sources & evidence

ORD record
ord-b1c50b2198d040ed96f4ca0ec96744ab
Source dataset
uspto-grants-2012_01
Patent number
US08093273B2

Reaction notes

Loading…