Triethylene glycol monomethyl ether → 4-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)phthalonitrile

HRID 39208

反応式

HRID 39208 の反応式
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH3:14][O:15][CH2:16][CH2:17][O:18][CH2:19][CH2:20][O:21][CH2:22][CH2:23][O:24][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

参加物

5

反応物 3

HCID 8178Triethylene glycol monomethyl etherHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

生成物 1

HCID 190655314-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)phthalonitrile収率 45%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 4-nitrophthalonitrile (1.73 g, 10 mmol), triethylene glycol monomethyl ether (1.52 g, 10 mmol) and dried potassium carbonate (2.76 g, 20 mmol) in anhydrous DMF (15 mL) was stirred overnight at ambient temperature under argon. The solvents were removed in vacuo, and the crude product was purified by column chromatography on silica gel using dichloromethane/methanol mixture (97:3) as an eluent to give the product in 45% yield. [1H NMR (δ, ppm, CDCl3): 7.70 (d, 1H, J=8.7 Hz), 7.31 (d, 1H, J=2.5 Hz), 7.23 (dd, 1H, J=8.7 Hz, J=2.5 Hz), 4.22 (m, 2H), 3.88 (m, 2H), 3.6-3.75 (m, 6H), 3.53 (m, 2H), 3.37 (s, 3H).]

後処理

  1. customThe solvents were removed in vacuo
  2. customthe crude product was purified by column chromatography on silica gel
  3. customto give the product in 45% yield

出典と根拠

ORDレコード
ord-128614155516453eb32cc2eb5f74fba1
出典データセット
uspto-grants-2013_09
特許番号
US08524891B2

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