Sodium Hydroxide → (R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine

HRID 3932노트

반응식

HRID 3932 반응식
[OH-].[Na+].[OH:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=2)=[CH:6][CH:5]=1.Br[CH2:25][CH2:26][CH2:27][C@H:28]([CH3:35])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>O>[CH3:35][C@H:28]([CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:27][CH2:26][CH2:25][O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[CH:12][N:11]=2)=[CH:8][CH:9]=1

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 1725484Phenol, 4-(5-octyl-2-pyridinyl)-HCID 14069923(R)-1-bromo-(4-methyl)decane

생성물 1

HCID 14069925(R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine수율 47.1%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

20 ml of a 30% aqueous solution of sodium hydroxide was added dropwise to a mixture of 2 g (0.007 mol) of 2-(p-hydroxyphenyl)-5-octylpyridine and 1.65 g (0.007 mol) of (R)-1-bromo-(4-methyl)decane with stirring. The resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours. 150 ml of water was added to the reaction solution and the organic layer was extracted with chloroform. After washing the extract three times with water, chloroform was removed by distillation. The residue was chromatographed over 2.5×100 (cm) of silica gel and developed with hexane and benzene. The effluent was repeatedly recrystallized from a mixture of methanol and acetone to yield 1.44 g (0.0033 mol) of (R)2-[p-(4-methyldecyloxy)phenyl]-5-octylpyridine.

후처리

  1. temperatureThe resulting solution was heated to a temperature between about 90° and 100° C. for 3 hours
  2. extractionthe organic layer was extracted with chloroform
  3. washAfter washing the
  4. extractionextract three times with water, chloroform
  5. customwas removed by distillation
  6. customThe residue was chromatographed over 2.5×100 (cm) of silica gel
  7. customThe effluent was repeatedly recrystallized from a mixture of methanol and acetone

출처 및 근거

ORD 기록
ord-db779db8732644f49d9a577c43124856
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04723018

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