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

HRID 965288ノート

反応式

HRID 965288 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)C[C:19]1=O.C(=O)C1C=CC=CC=1.CN(C)CCN(C)C.C([Li])CCC.IC>O1CCCC1.O>[CH3:19][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 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 321710OxindoleHCID 3473283-Benzyl-1,3-dihydroindol-2-oneHCID 178418339Butyllithium

生成物 1

HCID 190750293-methyl-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 (prepared from 1,3-dihydro-2H-indol-2-one (4 g, 18.25 mmol) 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. Iodomethane (2.84 g, 20 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-methyl-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-bf63acb498f54b1180ea0b669858ffc1
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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