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

HRID 276999

反応式

HRID 276999 の反応式
[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]

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d4bbcddc35d940329c4de3e04e94709e
出典データセット
uspto-grants-2002_03
特許番号
US06355648B1

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