Acetone → 7-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-one

HRID 1792315Notes

Reaction equation

HRID 1792315 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:13]3[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1.[C:21](=[O:24])([O-])[O-].[K+].[K+].[CH3:27][O:28][CH2:29]Cl.O.[CH3:32]C(C)=O>>[CH3:27][O:28][CH2:29][O:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:20])[C:7]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:32][O:24][CH3:21])=[CH:15][CH:14]=3)([CH3:12])[CH2:8][S:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 11430Potassium CarbonateHCID 22033294HCID 22033294, compound

Product 1

HCID 220332467-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-oneYield 99%

Procedure

To a solution of 7-hydroxy-3-(4-hydroxyphenyl)-3-methylthiochroman-4-one (1.92 g, 6.7 mmol) in dry acetone (200 ml) were added potassium carbonate (8.34 g, 60.42 mmol) and methoxymethyl chloride (3.04 ml, 40.28 mmol), which was then heated for 8 hours. Water was added thereto, and the resulting solution was extracted with ethyl acetate. Then, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=7:3 and 1:1) to give the title compound (2.50 g, yield 99%).

Workup

  1. temperaturewas then heated for 8 hours
  2. extractionthe resulting solution was extracted with ethyl acetate
  3. washThen, the organic layer was washed with water and saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ebda4027a69c42b3933bf0b65468a55e
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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