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

HRID 346197ノート

反応式

HRID 346197 の反応式
[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

参加物

5

反応物 2

HCID 12052TriethylsilaneHCID 14459942HCID 14459942、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3454b4059a7644dba3da555aa49bcefa
出典データセット
uspto-grants-1991_10
特許番号
US05061717

反応ノート

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