Hydrochloric Acid → HCID 69004882、化合物

HRID 230790

反応式

HRID 230790 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[CH3:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[C:29](OC)=[O:30].Cl>O.C1COCC1.CCCCCC>[O:30]=[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([C:20]([OH:22])=[O:21])=[CH:16][CH:15]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 7470P-Toluic AcidHCID 7912DiisopropylamineHCID 755692-CarbomethoxypyridineHCID 178418339Butyllithium

生成物 1

HCID 69004882HCID 69004882、化合物収率 11.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

A THF solution (50 mL) of diisopropylamine (12.6 mL) was cooled to 0° C., and a hexane (33 mL) solution of 2.6 M n-butyllithium was added thereto and stirred at that temperature for 10 minutes. Then this was cooled to −78° C., and a THF solution (15 mL) of 4-methylbenzenecarboxylic acid (2.3 g) was dropwise added thereto. The reaction liquid was stirred at −40° C. for 2.5 hours, and then a THF solution (4 mL) of methyl picolinate (2.0 g) was dropwise added thereto. The reaction solution was heated up to room temperature, and stirred for one day. Next, water was added to the reaction liquid, then controlled to have a pH of 4 with aqueous hydrochloric acid solution added thereto, and then extracted with ethyl acetate. The organic layer was dried with anhydrous sodium sulfate, concentrated under reduced pressure, and the resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1) to obtain the entitled compound (400 mg).

後処理

  1. customThe reaction liquid
  2. stirringwas stirred at −40° C. for 2.5 hours
  3. temperatureThe reaction solution was heated up to room temperature
  4. stirringstirred for one day
  5. additionadded
  6. extractionextracted with ethyl acetate
  7. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customthe resulting residue was purified through silica gel column chromatography (hexane/ethyl acetate=4/1)

出典と根拠

ORDレコード
ord-8df35751d93e4b309d88ce135b230de5
出典データセット
uspto-grants-2009_07
特許番号
US07566781B2

関連ノート

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