Diethyl suberate → Ethyl 7-ethoxycarbonyl-7-nicotinoylheptanoate

HRID 1980848

反応式

HRID 1980848 の反応式
[H-].[Na+].[C:3]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].[C:19](OCC)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1>CCOCC>[CH2:17]([O:16][C:3]([CH:4]([C:19](=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[N:22][CH:21]=1)[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:15])[CH3:18]

参加物

5

反応物 3

HCID 16301Diethyl suberateHCID 24758Sodium hydrideHCID 69188Ethyl Nicotinate

生成物 1

HCID 20400829Ethyl 7-ethoxycarbonyl-7-nicotinoylheptanoate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To a suspension of 16 g of 50% sodium hydride in 450 ml of ether is added dropwise 92.2 g of diethyl suberate and 27.3 ml (30.2 g) of ethyl nicotinate at room temperature, under nitrogen. The reaction mixture is heated at reflux temperature overnight, and, after cooling, 400 ml of ice water is added. The ether layer is separated (discarded) and the aqueous adjusted to pH 5 with 1N hydrochloric acid and extracted with ether (3×250 ml). The ether layer is dried and concentrated to give ethyl 7-ethoxycarbonyl-7-nicotinoylheptanoate as an oil. A solution of this ester in 300 ml of 1M sulfuric acid is heated for 12 hours at reflux temperature. The reaction solution is cooled by an ice bath and adjusted to pH=4.5-5.0 with saturated sodium bicarbonate solution. A white solid is collected and, after washing with water and air-drying, is recrystallized from ethanol to give 7-nicotinoylheptanoic acid, m.p. 113°-115°.

後処理

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux temperature overnight
  3. temperatureafter cooling
  4. customThe ether layer is separated (discarded)
  5. extractionextracted with ether (3×250 ml)
  6. dry with materialThe ether layer is dried
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1480dde3fe3e43ce92d91104272a8bf4
出典データセット
uspto-grants-1985_04
特許番号
US04511573

関連ノート

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