Benzaldehyde → 3-methylthio-3-phenylmethyl-1,3-dihydro-2H-indol-2-one

HRID 965286ノート

反応式

HRID 965286 の反応式
[C:1]1([CH2:7][CH:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C2C(=CC=CC=2)CC1=O.C(=O)C1C=CC=CC=1.CN(C)CCN(C)C.C([Li])CCC.[CH3:49][S:50]SC>O1CCCC1.O>[CH3:49][S:50][C:8]1([CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[NH:10][C:9]1=[O:17]

参加物

9

反応物 6

HCID 240BenzaldehydeHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 12232Dimethyl DisulfideHCID 321710OxindoleHCID 3473283-Benzyl-1,3-dihydroindol-2-oneHCID 178418339Butyllithium

生成物 1

HCID 190750183-methylthio-3-phenylmethyl-1,3-dihydro-2H-indol-2-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-75 °C

実験手順

3-Phenylmethyl-1,3-dihydro-2H-indol-2-one (4 g, 18.25 mmol) (prepared from 1,3-dihydro-2H-indol-2-one and benzaldehyde by the method of Daisley and Walker J. Chem. Soc. (C) (1971) page 1373) and tetramethylethylenediamine (4.5 g, 38.7 mmol) was dissolved in freshly distilled tetrahydrofuran under nitrogen and cooled to -75° C. in an acetone/dry ice bath. n-Butyllithium (2.5M, 20 ml, 50 mmol) was added and the mixture was stirred at -75° C. for 30 minutes. Dimethyl disulfide (1.65 g, 17.6 mmol) was added and the mixture was allowed to warm to room temperature. Water (5 ml) was added and the mixture was concentrated under reduced pressure to a yellow oil. Column chromatography on silica gel (eluent ethyl acetate/hexane) gave 3-methylthio-3-phenylmethyl-1,3-dihydro-2H-indol-2-one as a yellow oil which solidified on standing.

後処理

  1. temperatureto warm to room temperature
  2. concentrationthe mixture was concentrated under reduced pressure to a yellow oil

出典と根拠

ORDレコード
ord-53eec181e35b424398cbe06f4d07688c
出典データセット
uspto-grants-1998_06
特許番号
US05773448

反応ノート

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