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

HRID 639199노트

반응식

HRID 639199 반응식
[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]

참가 물질

7

반응물 2

HCID 68704275(2-Chloro-6-cyano-naphthalen-1-yl)-acetic acid ethyl esterHCID 178527019HCID 178527019, 화합물

생성물 1

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

시약·촉매·용매 4

HCID 935Nickel촉매HCID 176Acetic Acid용매HCID 962Water용매HCID 1049Pyridine용매

반응 조건

온도
100 °C

실험 절차

(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]−.

후처리

  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)

출처 및 근거

ORD 기록
ord-f0de6e7233494d6f95a4e1d6d9cdf2f4
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691861B2

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