Methyl iodide → 7-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one

HRID 1859311Notes

Reaction equation

HRID 1859311 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:21])[CH:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)[CH2:9][S:10]2)=[CH:5][CH:4]=1.O1CCC[CH2:23]1.C([N-]C(C)C)(C)C.[Li+].CI>O>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:21])[C:8]([C:13]3[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=3)([CH3:23])[CH2:9][S:10]2)=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8028TetrahydrofuranHCID 2724682Lithium diisopropylamideHCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-one

Product 1

HCID 109799547-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-oneYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (725 mg, 2.41 mmol) obtained in Example 25 was added dry tetrahydrofuran (30 ml). Then lithium diisopropylamide (2.41 ml, 4.83 mmol, 2.0 mol hexane/tetrahydrofuran solution) was added dropwise thereto at -78° C. The reaction mixture was stirred for 45 minutes and methyl iodide (7.5 ml, 120.6 mmol) was added thereto. The reaction solution was stirred for one hour at -78° C. and for 24 hours at -10° C. and, after adding water, extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=9:1) to obtain 550 mg (yield: 72%) of the title compound as a yellow solid.

Workup

  1. customat -78° C
  2. stirringThe reaction solution was stirred for one hour at -78° C. and for 24 hours at -10° C.
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-ccf99860494945ac8f5daa773a8ac1cf
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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