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

HRID 965288노트

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HRID 965288 반응식
[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]

참가 물질

9

반응물 6

HCID 240BenzaldehydeHCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 321710OxindoleHCID 3473283-Benzyl-1,3-dihydroindol-2-oneHCID 178418339Butyllithium

생성물 1

HCID 190750293-methyl-3-phenylmethyl-1,3-dihydro-2H-indol-2-one

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
-75 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-bf63acb498f54b1180ea0b669858ffc1
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05773448

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