Diisopropylamine → 4-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine

HRID 993281

反応式

HRID 993281 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[N:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[CH:29]=[O:30])[CH2:24][CH2:23][CH2:22][CH2:21]1.[Cl-].[NH4+]>O1CCCC1>[CH:20]1([O:25][C:26]2[CH:27]=[C:28]([CH:29]([OH:30])[CH2:19][C:16]3[CH:17]=[CH:18][N:13]=[CH:14][CH:15]=3)[CH:31]=[CH:32][C:33]=2[O:34][CH3:35])[CH2:21][CH2:22][CH2:23][CH2:24]1

参加物

7

反応物 5

HCID 7912DiisopropylamineHCID 79634-MethylpyridineHCID 25517Ammonium ChlorideHCID 27358933-Cyclopentyloxy-4-methoxybenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 221458574-[2-(3-Cyclopentyloxy-4-methoxyphenyl)-2-hydroxyethyl]pyridine収率 91.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A stirred solution of diisopropylamine (14 mL) in dry tetrahydrofuran (150 mL), is treated dropwise with a solution of butyl lithium in hexanes (40 mL; 2.5 M), under nitrogen, while keeping the temperature at below −70° C. The resulting mixture is then stirred for a further period of 30 minutes at below −70° C. The stirred mixture, while it is still maintained at below −70° C., is then treated dropwise with a solution of 4-picoline (9.3 g) in dry tetrahydrofuran (20 mL). The stirred mixture is maintained at below −70° C. for a further 45 minutes. The stirred mixture, while it is still maintained at below −70° C., is then treated with a solution of 3-cyclopentyloxy-4-methoxybenzaldehyde (22.0 g) in dry tetrahydrofuran (100 mL), and it is stirred at below −70° C. for a further 30 minutes. The resulting mixture is then allowed to warm to room temperature overnight, and then treated with saturated aqueous ammonium chloride solution (200 mL). The layers are separated and the aqueous layer is further extracted with ethyl acetate (3×300 mL). The combined organic extracts are dried over magnesium sulfate and evaporated to dryness. The resulting residue is recrystallized from ethyl acetate, to give (±)-1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(pyrid-4-yl)ethanol (28.5 g), in the form of a cream solid, m.p. 102-103° C.

後処理

  1. customat below −70° C
  2. temperatureThe stirred mixture, while it is still maintained at below −70° C.
  3. temperatureThe stirred mixture is maintained at below −70° C. for a further 45 minutes
  4. temperatureThe stirred mixture, while it is still maintained at below −70° C.
  5. stirringis stirred at below −70° C. for a further 30 minutes
  6. customThe layers are separated
  7. extractionthe aqueous layer is further extracted with ethyl acetate (3×300 mL)
  8. dry with materialThe combined organic extracts are dried over magnesium sulfate
  9. customevaporated to dryness
  10. customThe resulting residue is recrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-ae40188fd06047608204c386d1d721e4
出典データセット
uspto-grants-2002_10
特許番号
US06472412B1

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