Iodoethane → 3,3-diethyl-2,3-dihydro-1H-indol-2-one

HRID 9327

반응식

HRID 9327 반응식
[CH2:1]([C:3]1[C:4](=[O:12])[N:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2)[CH3:2].[CH2:13]([Li])[CH2:14]CC.CN(C)CCN(C)C.ICC.[NH4+].[Cl-]>C1COCC1>[CH2:1]([C:3]1([CH2:13][CH3:14])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[NH:5][C:4]1=[O:12])[CH3:2]

참가 물질

7

반응물 5

HCID 6340IodoethaneHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 219862793-Ethylindol-2-oneHCID 178418339Butyllithium

생성물 1

HCID 151532213,3-diethyl-2,3-dihydro-1H-indol-2-one수율 47.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 3-ethyl-indol-2-one (16 g, 0.1 mol) in dry THF (200 ml) under N2 was cooled to −25° C. and treated drop wise with n-butyllithium (2.5M in hexanes, 80 ml, 0.2 mol). To the resulting solution was added N,N,N′,N′-tetramethylethylenediamine (30 ml, 0.2 mol). After 30 min. iodoethane (8 ml, 0.1 mol) was added and the reaction mixture was allowed to warm to RT and stirred over night. The reaction mixture was poured into an aqueous NH4Cl solution, extracted with EtOAc (2×) and the combined organic layers were washed with dil. HCl, water, brine, dried (MgSO4) and concentrated. The residual oil was triturated with hexane to afford 3,3-diethylindol-2-one (9 g, 45%), m.p. 156–159° C.; 1H NMR (DMSO-d6) δ 10.44 (s, 1H), 7.70–7.69 (t, 1H), 7.62–7.59 (m, 1H), 7.58 (d, 1H J=1.7 Hz), 7.53–7.50 (m, 1H), 7.45–7.41 (t, 1H), 7.36–7.35 (m, 1H), 7.34–7.33 (m, 1H), 6.91–6.89 (d, 1H J=8.2 Hz), 1.87–1.80 (m, 2H), 1.77–1.70 (m, 2H), 0.54–0.50 (t, 6H); MS/ (+ESI) m/z 190 (M+H).

후처리

  1. extractionextracted with EtOAc (2×)
  2. washthe combined organic layers were washed with dil. HCl, water, brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual oil was triturated with hexane

출처 및 근거

ORD 기록
ord-2b44cd7d278c4cc8bad2b58a6a049672
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091234B2

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