Tetrahydrofuran → 1-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

HRID 1362351ノート

反応式

HRID 1362351 の反応式
C([Li])(C)(C)C.C1C[O:9][CH2:8]C1.[CH2:11]([O:13][CH:14]([O:26][CH2:27][CH3:28])[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]#[N:25])=[CH:16]1)[CH3:12]>CN(C=O)C>[CH2:11]([O:13][CH:14]([O:26][CH2:27][CH3:28])[N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24]#[N:25])=[C:16]1[CH:8]=[O:9])[CH3:12]

参加物

5

反応物 3

HCID 8028TetrahydrofuranHCID 592776081-diethoxymethyl-1H-indole-3-carbonitrileHCID 178418306HCID 178418306、化合物

生成物 1

HCID 592776141-diethoxymethyl-2-formyl-1H-indole-3-carbonitrile

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
10 °C

実験手順

tert-Butyl lithium (18.1 mL, 31 mmol, 1.7M in pentane) was added to a THF (100 mL) solution of 1-diethoxymethyl-1H-indole-3-carbonitrile (6.83 g, 28 mmol) at −78° C. The mixture was warmed to 10° C., stirred for 30 min at this temperature, cooled to −78° C. and heated with DMF (20 mL). The mixture was warmed to 10° C., stirred for 30 min at this temperature, cooled to −78° C. and quenched with a saturated aqueous solution of NaHCO3. The resulting mixture was treated with ether (200 mL); the organic layer was washed with water and brine, dried and evaporated to dryness. NMR (300 MHz, CDCl3, δ): 10.24 (s, 1H), 8.10 (d, J=7.7 Hz, 1H), 7.91 (d, J=7.7 Hz, 1H), 7.53 (t, J=7.7 Hz, 1H), 7.43 (t, J=7.5 Hz, 1H), 7.34 (s, 1H), 3.80 (m, 2H), 3.52 (m, 2H), 1.26 (t, J=6.4 Hz, 1H).

後処理

  1. temperaturecooled to −78° C.
  2. temperatureThe mixture was warmed to 10° C.
  3. stirringstirred for 30 min at this temperature
  4. temperaturecooled to −78° C.
  5. customquenched with a saturated aqueous solution of NaHCO3
  6. additionThe resulting mixture was treated with ether (200 mL)
  7. washthe organic layer was washed with water and brine
  8. customdried
  9. customevaporated to dryness

出典と根拠

ORDレコード
ord-50e8694dfb684d059913e92034821cd1
出典データセット
uspto-grants-2011_02
特許番号
US07879872B2

反応ノート

読み込み中…