تفاعل #424440

ord-266f456e38fa4eac88f404e48577250d

معادلة التفاعل

Cc1ccc(CC#N)cc1O
2-(3-Hydroxy-4-methylphenyl)acetonitrile
O=C([O-])[O-].[K+].[K+]
K2CO3
Cc1cccc(C)c1CCl
2,6-Dimethylbenzyl chloride
Cc1ccc(CC#N)cc1OCc1c(C)cccc1C
title compound
Cc1ccc(CC#N)cc1OCc1c(C)cccc1C
2-(3-(2,6-dimethylbenzyloxy)-4-methylphenyl)acetonitrile

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    غسيلwashed with water (20 ml) and brine
  2. 2
    تجفيفThe organic layer was dried over Na2SO4
  3. 3
    ترشيحfiltered
  4. 4
    تركيزconcentrated
  5. 5
    أخرىpurified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1)

الإجراء التجريبي

To a stirred solution of 2-(3-Hydroxy-4-methylphenyl)acetonitrile (Step A, 2.18 g, 14.8 mmol), K2CO3 (2.66 g, 19.2 mmol) in dry DMF (20 ml) was added 2,6-Dimethylbenzyl chloride (2.97 g, 19.2 mmol) at room temperature under argon. The reaction mixture was stirred for 16 hours, diluted with EtOAc (40 ml), washed with water (20 ml) and brine. The organic layer was dried over Na2SO4, filtered, concentrated, and purified by flash chromatography on a silica gel column (hex: ethyl acetate 2:1) to give the title compound as a white solid.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US08889724B2uspto-grants-2014_11