Sodium hydride → 2-Chlorobenzenesulfonic acid 3-[5-cyanopentyloxy]-5-methylphenyl ester

HRID 368547

反応式

HRID 368547 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:5]=[C:6]([O:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1.Br[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[N:29]>CN(C)C=O>[C:28]([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:3][C:4]1[CH:5]=[C:6]([O:11][S:12]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[Cl:21])(=[O:14])=[O:13])[CH:7]=[C:8]([CH3:10])[CH:9]=1)#[N:29]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 810936-BromohexanenitrileHCID 112779473-(2-Chlorophenylsulfonyloxy)-5-methylphenol

生成物 1

HCID 540336022-Chlorobenzenesulfonic acid 3-[5-cyanopentyloxy]-5-methylphenyl ester収率 74.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (24 mg, 1 mmol; 100%) was added to solution of 250 mg (0.855 mmol) of 2-chlorobenzenesulfonic acid 3-hydroxy-5-methylphenyl ester, as prepared in step (c) of Example 1, in 2 mL of N,N-dimethylformamide. After 5 min, 130 μL (0.93 mmol) of 6-bromohexanenitrile was added to the reaction mixture. The reaction mixture was stirred for 2 h at ambient temperature, quenched with brine (50 mL), extracted into diethyl ether (50 mL), washed with water (3×10 mL), dried (MgSO4), and concentrated in vacuo. The residue was purified by flash chromatography (methylene chloride/petroleum ether 4:1 to 100:0) to give 250 mg of the title compound as a colorless oil which solidified upon standing. 1H-NMR (300 MHz, CDCl3) δ 7.97 (dd, 1 H, J=1.4, 7.8 Hz), 7.56-7.65 (m, 2 H), 7.36-7.41 (m, 1 H), 6.59 (br s, 1 H), 6.53 (br, s 1 H), 6.48 (t, 1 H, J=1.1 Hz), 3.85 (t, 2 H), 2.38 (t, 2 H), 2.24 (s, 3 H), and 1.6-1.8 (m, 6 H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C19H20NClO4S: 416.1 (M+Na). Found: 416.1.

後処理

  1. customquenched with brine (50 mL)
  2. extractionextracted into diethyl ether (50 mL)
  3. washwashed with water (3×10 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash chromatography (methylene chloride/petroleum ether 4:1 to 100:0)

出典と根拠

ORDレコード
ord-571f359d64284342960805b629a5f196
出典データセット
uspto-grants-2000_10
特許番号
US06133315

関連ノート

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