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Benzene → 5-[4-(6-Hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-yl-methoxy)benzyl]thiazolidine-2,4-dione

HRID 1030372
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HRID 1030372 반응식
O[CH:2]1[C:11]2[C:6](=[C:7]([CH3:15])[C:8]([CH3:14])=[C:9]([OH:13])[C:10]=2[CH3:12])[O:5][C:4]([CH2:17][O:18][C:19]2[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=2)([CH3:16])[CH2:3]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>CN(C)C=O>[OH:13][C:9]1[C:10]([CH3:12])=[C:11]2[C:6](=[C:7]([CH3:15])[C:8]=1[CH3:14])[O:5][C:4]([CH2:17][O:18][C:19]1[CH:32]=[CH:31][C:22]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:20]=1)([CH3:16])[CH:3]=[CH:2]2
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참가 물질

5

반응물 3

HCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 136058355-[4-(4,6-Dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione

생성물 1

HCID 150938375-[4-(6-Hydroxy-2,5,7,8-tetramethyl-2H-chromen-2-yl-methoxy)benzyl]thiazolidine-2,4-dione

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 140 mg of 5-[4-(4,6-dihydroxy-2,5,7,8-tetramethylchroman-2-ylmethoxy)benzyl]thiazolidine-2,4-dione (prepared as described in Example 30), 10 mg of p-toluenesulfonic acid, 10 ml of benzene and 0.5 ml of dimethylformamide was heated under reflux for 1 hour. The reaction solution was cooled, washed with a saturated aqueous solution of sodium bicarbonate and then with water and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by silica gel column chromatography eluted with a 4:1 by volume mixture of benzene and ethyl acetate, to give the title compound, softening at 173°-176° C.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe reaction solution was cooled
  4. washwashed with a saturated aqueous solution of sodium bicarbonate
  5. dry with materialwith water and dried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe residue was purified by silica gel column chromatography
  8. washeluted with a 4:1 by volume mixture of benzene and ethyl acetate

출처 및 근거

ORD 기록
ord-af3dcb2bd82641cbb3fecccbf0e221e1
출처 데이터셋
uspto-grants-1992_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05104888

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