Methoxymethyl-triphenylphosphonium chloride → 4-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester

HRID 658305ノート

反応式

HRID 658305 の反応式
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:30][O:31][C:32](=[O:47])[C:33]1[CH:38]=[CH:37][C:36]([C:39](=O)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH3:30][O:31][C:32](=[O:47])[C:33]1[CH:38]=[CH:37][C:36]([C:39](=[CH:2][O:3][CH3:4])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:34]=1

参加物

5

反応物 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 598693704-Heptanoyl-benzoic acid methyl ester

生成物 1

HCID 684911714-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

(Methoxymethyl)triphenylphosphonium chloride (10.34 g, 30.24 mmol) is suspended in anhydrous toluene (75 mL) and potassium tert-butoxide (3.39 g, 30.24 mmol) is carefully added. The solution is allowed to stir at room temperature for 4 h. 4-Heptanoyl-benzoic acid methyl ester (5.0 g, 20.16 mmol) is then dissolved in anhydrous toluene (25 mL) and added to the reaction mixture by cannula. The reaction is allowed to stir at room temperature overnight and is monitored by TLC. Upon complete consumption of starting material, the reaction is carefully quenched with saturated ammonium chloride solution, extracted with diethyl ether, washed, dried, and concentrated. The title compound is purified by column chromatography using hexanes/ethyl acetate and used directly in the next step.

後処理

  1. additionadded to the reaction mixture by cannula
  2. stirringto stir at room temperature overnight
  3. customUpon complete consumption of starting material
  4. customthe reaction is carefully quenched with saturated ammonium chloride solution
  5. extractionextracted with diethyl ether
  6. washwashed
  7. customdried
  8. concentrationconcentrated
  9. customThe title compound is purified by column chromatography

出典と根拠

ORDレコード
ord-e627c22587b94daa994910e9c163ac31
出典データセット
uspto-grants-2011_12
特許番号
US08076374B2

反応ノート

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