Potassium Carbonate → 7-Methoxy-3-(4-methoxyphenyl)thiochroman-4-one

HRID 1859337ノート

反応式

HRID 1859337 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH2:13][S:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)[C:10]([OH:12])=O)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].P(Cl)(Cl)(Cl)=O>C(#N)C>[CH3:22][O:21][C:17]1[CH:16]=[C:15]2[C:20]([C:10](=[O:12])[CH:9]([C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=3)[CH2:13][S:14]2)=[CH:19][CH:18]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 10969180HCID 10969180、化合物

生成物 1

HCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-one

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
60 °C

実験手順

To acetonitrile solution (120 ml) of 2-(4-methoxyphenyl)-3-(3-methoxyphenylthio)propionic acid (4) (12.8 g, 40.3 mmol) obtained above was added potassium carbonate (1.59 g, 11.5 mmol) and phosphorus oxychloride (18.7 ml, 200 mmol) at 0° C. and then stirred for 18 hours at 60° C. The reaction solution was quenched with ice-water and extracted with ether. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate and then distilled under reduced pressure to remove the solvent. The obtained crude product was washed with ether to obtain 6.8 g of the first crop of 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (5). Further, the filtrate was concentrated and the residue was then purified with silica gel column chromatography (ethyl acetate:hexane=1:3) to obtain 1.0 g of the second crop of 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (5) (total yield: 7.8 g, 65%). NMR data of the compound (5) was identical to that described in Example 25.

後処理

  1. customThe reaction solution was quenched with ice-water
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationdistilled under reduced pressure
  6. customto remove the solvent
  7. customThe obtained crude product
  8. washwas washed with ether

出典と根拠

ORDレコード
ord-0ad73b2939144917845e6748e62f173b
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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