Sodium Hydroxide → methyl 3-formyl-1H-indole-4-carboxylate

HRID 33281

反応式

HRID 33281 の反応式
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([O:12][CH3:13])=[O:11])[C:4]=2[CH:3]=[CH:2]1.O=P(Cl)(Cl)Cl.CN([CH:22]=[O:23])C.CC([O-])=O.[Na+].[OH-].[Na+]>ClC(Cl)C>[CH:22]([C:3]1[C:4]2[C:5]([C:10]([O:12][CH3:13])=[O:11])=[CH:6][CH:7]=[CH:8][C:9]=2[NH:1][CH:2]=1)=[O:23]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 2733668methyl 1H-indole-4-carboxylateHCID 13765457DMF Phosphorus oxychloride

生成物 1

HCID 12396096methyl 3-formyl-1H-indole-4-carboxylate

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

反応条件

温度
50 °C

実験手順

A solution of methyl indole-4-carboxylate (250 mg, 1.43 mmol) in dichloroethane (2 mL) was treated with a solution of POCl3-DMF (1.5 equivalent (eq)) at room temperature (rt). The orange solution was heated at 50° C. for 1 hour. The reaction solution was poured into ice-cold aqueous (aq.) NaOAc (1 g in 2 mL), the aqueous solution was adjusted to pH=8 with 1M NaOH, and extracted with EtOAc (10 mL×3). The organic solution was washed with water and brine, dried (Na2SO4), filtered, and concentrated to give methyl 3-formyl-indole-4-carboxylate as an oil, 271 mg (93%). 1H NMR (300 MHz, d6-DMSO) δ 3.68 (s, 3H), 7.16 (t, 1H, J=7.8 Hz), 7.40 (dd, 1H, J=7.8, 0.8 Hz), 7.56 (d, 1H, J=7.8, 0.8 Hz), 8.16 (d, 1H, J=3.2 Hz), 10.00 (s, 1H), 12.30 (br s, 1H).

後処理

  1. extractionextracted with EtOAc (10 mL×3)
  2. washThe organic solution was washed with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-bb23c307690b48c8b2b7e1c1418720d0
出典データセット
uspto-grants-2008_09
特許番号
US07429578B2

関連ノート

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