1,2-Dimethoxyethane → 4-(4-Cyanonaphthalene-2-yl)benzoic acid methyl ester

HRID 2383345ノート

反応式

HRID 2383345 の反応式
Cl[C:2]1[CH:11]=[C:10]([C:12]#[N:13])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)N=1.[CH3:14][O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21](B(O)O)=[CH:20][CH:19]=1)=[O:17].[C:27](=O)([O-])[O-].[Na+].[Na+].C(COC)OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C(OCC)(=O)C.O>[CH3:14][O:15][C:16](=[O:17])[C:18]1[CH:23]=[CH:22][C:21]([C:2]2[CH:11]=[C:10]([C:12]#[N:13])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[CH:27]=2)=[CH:20][CH:19]=1

参加物

8

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 228320822-Chloroquinoline-4-carbonitrile

生成物 1

HCID 673093094-(4-Cyanonaphthalene-2-yl)benzoic acid methyl ester収率 39.4%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
150 °C

実験手順

2-Chloroquinoline-4-carbonitrile (0.20 g), 4-methoxycarbonylphenylboronic acid (0.21 g), tetrakis(triphenylphosphine)palladium (0.061 g) and sodium carbonate (0.22 g) were suspended in a mixed solvent of dimethoxyethane (2 mL) and water (0.5 mL), and the resulting mixture was stirred at 150° C. for 30 minutes using microwave reactor (Biotage). To the reaction mixture was added ethyl acetate, and the reaction mixture was filtered through a Celite pad. The filtrate was poured into water, and the organic layer was washed with water and brine. The organic layer was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34) to give 4-(4-cyanonaphthalene-2-yl)benzoic acid methyl ester (0.12 g). To a solution of this compound (0.12 g) in a mixed solvent of tetrahydrofuran (2 mL), ethanol (1 mL) and water (1 mL) was added lithium hydroxide monohydrate (0.14 g), and the mixture was stirred at room temperature overnight. To the reaction mixture was added 2 mol/L hydrochloric acid (0.35 mL). The precipitated solid was collected by filtration, washed with methanol, and dried under reduced pressure to give the title compound (0.024 g).

後処理

  1. filtrationthe reaction mixture was filtered through a Celite pad
  2. additionThe filtrate was poured into water
  3. washthe organic layer was washed with water and brine
  4. concentrationThe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=100/0-66/34)

出典と根拠

ORDレコード
ord-fddb9602b6c8482aacef12b5688698e4
出典データセット
uspto-grants-2012_09
特許番号
US08263622B2

反応ノート

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