Triethylsilane → 5-{[4-(3-Phenylpropanoyl)phenyl]methyl}-1,3-thiazolidine-2,4-dione

HRID 1588755노트

반응식

HRID 1588755 반응식
[C:1]1(/[CH:7]=[CH:8]/[C:9]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.O>[C:1]1([CH2:7][CH2:8][C:9]([C:11]2[CH:24]=[CH:23][C:14]([CH2:15][CH:16]3[S:20][C:19](=[O:21])[NH:18][C:17]3=[O:22])=[CH:13][CH:12]=2)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 14459942HCID 14459942, 화합물

생성물 1

HCID 144599135-{[4-(3-Phenylpropanoyl)phenyl]methyl}-1,3-thiazolidine-2,4-dione수율 82.4%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매

반응 조건

온도
0 °C

실험 절차

To an ice-cooled solution of the title product of Example 39 (2.0 g, 5.9 mmol) in trifluoroacetic acid (20 ml) was added triethylsilane (0.95 ml, 5.9 mmol). The mixture was stirred for 25 minutes at 0° C., then diluted with water (50 ml) and extracted with ether (2×40 ml). The combined extracts were washed with water (2×40 ml) and 5% sodium bicarbonate (2×40 ml), dried over sodium sulfate and concentrated in vacuo. The residue was triturated with hexane to give present title product as a pale yellow solid (1.65 g, 82%); m.p. 119°-121° C.

후처리

  1. extractionextracted with ether (2×40 ml)
  2. washThe combined extracts were washed with water (2×40 ml) and 5% sodium bicarbonate (2×40 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was triturated with hexane

출처 및 근거

ORD 기록
ord-1cc9223804cf4abe8cdb60d0c359780c
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05223522

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