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

HRID 1859337노트

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HRID 1859337 반응식
[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

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 10969180HCID 10969180, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0ad73b2939144917845e6748e62f173b
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153768

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