(2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl ester → (2-Chloro-6-formyl-naphthalen-1-yl)-acetic acid ethyl ester

HRID 639199ノート

反応式

HRID 639199 の反応式
[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([C:16]#N)=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:18])[CH3:2].[PH2]([O-])=[O:21].[Na+]>O.N1C=CC=CC=1.C(O)(=O)C.[Ni]>[CH2:1]([O:3][C:4](=[O:19])[CH2:5][C:6]1[C:15]2[C:10](=[CH:11][C:12]([CH:16]=[O:21])=[CH:13][CH:14]=2)[CH:9]=[CH:8][C:7]=1[Cl:18])[CH3:2]

参加物

7

反応物 2

HCID 68704275(2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl esterHCID 178527019HCID 178527019、化合物

生成物 1

HCID 86623397(2-Chloro-6-formyl-naphthalen-1-yl)-acetic acid ethyl ester

試薬・触媒・溶媒 4

HCID 935Nickel触媒HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 1049Pyridine溶媒

反応条件

温度
100 °C

実験手順

(2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl ester (1.39 g, 5.07 mmol) is dissolved in a mixture of water (17 ml), pyridine (33 ml) and glacial acetic acid (17 ml). Sodium hypophosphite (4.30 g, 40.62 mmol) and Raney nickel (3.2 g) are then added at RT. The reaction mixture is heated to 100° C. for 1 h. TLC analysis indicates complete consumption of starting material. The reaction mixture is cooled to RT and filtered through Celite. After addition of silica gel, the solvents are removed on a rotary evaporator. Purification by FCC (hexane/EtOAc 5:1) yields the title compound. 1H NMR (CDCl3, 400 MHz): δ 1.17 (t, J=8 Hz, 3H), 4.10 (q, J=8 Hz, 2H), 4.24 (s, 2H), 7.52 (d, J=10 Hz, 1H), 7.82 (d, J=10 Hz; 1H), 7.94-7.98 (m, 2H); 8.26 (s, 1H), 10.09 (s, 1H). ES−-MS: 275.2, 277.3 [M−H]−.

後処理

  1. customconsumption of starting material
  2. temperatureThe reaction mixture is cooled to RT
  3. filtrationfiltered through Celite
  4. additionAfter addition of silica gel
  5. customthe solvents are removed on a rotary evaporator
  6. customPurification by FCC (hexane/EtOAc 5:1)

出典と根拠

ORDレコード
ord-f0de6e7233494d6f95a4e1d6d9cdf2f4
出典データセット
uspto-grants-2010_04
特許番号
US07691861B2

反応ノート

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