تفاعل #1787

ord-4b7921c79135478487a5a927dd9e4a45

معادلة التفاعل

CCOC(=O)c1c(C)ccnc1C
2,4-dimethyl-3-carboethoxypyridine
[Al+3].[H-].[H-].[H-].[H-].[Li+]
lithium aluminum hydride
Cc1ccnc(C)c1CO
2,4-dimethyl-3-hydroxymethylpyridine

الكواشف

لا شيء

المذيبات

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةthen cooled to 0° C.
  2. 2
    أخرىquenched with EtOAc (2.5 mL)
  3. 3
    ترشيحThe solution was filtered
  4. 4
    أخرىthe solvent removed under reduced pressure

الإجراء التجريبي

The 2,4-dimethyl-3-carboethoxypyridine (11.3 g, 63.1 mmol) in distilled THF (375 mL) under nitrogen was cooled to 0° C. and lithium aluminum hydride (1M in THF, 63.1 mL) was added dropwise. The reaction was stirred for 18 hours at room temperature then cooled to 0° C. and quenched with EtOAc (2.5 mL), then H2O (2.5 mL), then 15% NaOH (2.5 mL), followed by H2O (7.5 mL). The solution was filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-hydroxymethylpyridine.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US05726172uspto-grants-1998_03