2,5-Hexanediol → 2-Chloro-4-(4-hydroxy-1-methyl-pentyloxy)-benzonitrile

HRID 2103743

反応式

HRID 2103743 の反応式
[CH3:1][CH:2]([OH:8])[CH2:3][CH2:4][CH:5]([OH:7])[CH3:6].[O-]CCCC.[K+].[Cl:15][C:16]1[CH:23]=[C:22](F)[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]>O1CCCC1>[Cl:15][C:16]1[CH:23]=[C:22]([O:7][CH:5]([CH3:6])[CH2:4][CH2:3][CH:2]([OH:8])[CH3:1])[CH:21]=[CH:20][C:17]=1[C:18]#[N:19]

参加物

5

反応物 3

HCID 180492,5-HexanediolHCID 1090002-Chloro-4-fluorobenzonitrileHCID 23699084Potassium butoxide

生成物 1

HCID 113458042-Chloro-4-(4-hydroxy-1-methyl-pentyloxy)-benzonitrile収率 46.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2,5-hexanediol (28 mg, 0.240 mmol) in tetrahydrofuran was added an excess of potassium butoxide. The admixture was stirred, briefly, and 2-chloro-4-fluoro-benzonitrile (37 mg, 0.240 mmol) was added. The admixture was stirred at room temperature for 72 hours. Purification by reverse phase high pressure chromatography eluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water) provided 28.4 mg of 2-chloro-4-(4-hydroxy-1-methyl-pentyloxy)-benzonitrile. 1H NMR (CDCl3) δ 7.50 (d, 1H), 6.95 (m, 1H), 6.79 (br d, 1H), 4.43 (m, 1H), 3.79 (m, 1H), 1.89-1.40 (m, 4H), 1.30 (d, 3H), 1.17 (d, 3H); MS m/z 253.

後処理

  1. stirringThe admixture was stirred at room temperature for 72 hours
  2. customPurification by reverse phase high pressure chromatography
  3. washeluting with a solvent gradient (15% of 0.1% formic acid/CH3CN in 0.1% formic acid/water to 100% of 0.1% formic acid/water)

出典と根拠

ORDレコード
ord-375f062679cc4cda8e18fb7ffbbe9e19
出典データセット
uspto-grants-2009_08
特許番号
US07576128B2

関連ノート

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