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

HRID 1859311ノート

反応式

HRID 1859311 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-ccf99860494945ac8f5daa773a8ac1cf
出典データセット
uspto-grants-2000_11
特許番号
US06153768

反応ノート

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