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

HRID 651539

반응식

HRID 651539 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a32060e5af8244bdbee14082aca3e1e9
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281206B1

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