Water → Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate

HRID 491833ノート

反応式

HRID 491833 の反応式
[H-].[Na+].[CH:3]([N:6]1[CH2:11][CH2:10][CH:9]([CH:12]=O)[CH2:8][CH2:7]1)([CH3:5])[CH3:4].[OH2:14].[O:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1>C(OCC)C>[CH:3]([N:6]1[CH2:7][CH2:8][CH:9]([CH:12]=[CH:17][C:16]([O:15][CH2:19][CH3:18])=[O:14])[CH2:10][CH2:11]1)([CH3:4])[CH3:5]

参加物

6

反応物 4

HCID 962WaterHCID 8028Tetrahydrofuran2 回HCID 24758Sodium hydrideHCID 178939231-Isopropyl-piperidine-4-carboxaldehyde

生成物 1

HCID 68453328Ethyl 3-(1-isopropylpiperidin-4-yl)acrylate

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

Triethyl phosphonoacetate (7.96 g) is dissolved in tetrahydrofuran (50 ml) and thereto is added gradually 60% sodium hydride in oil (1.45 g) under ice-cooling. After stirring for 20 minutes under ice-cooling, to the mixture is added 1-isopropylpiperidine-4-carbaldehyde (5.03 g) obtained in Reference Example 134(2) in tetrahydrofuran (25 ml). The reaction solution is stirred for 3 hours, diluted with diethyl ether, thereto is added water and the mixture is extracted with ethyl acetate. The organic layer is washed with water and saturated brine, dried over sodium sulfate and evaporated to remove the solvent under reduced pressure. The resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1) to give ethyl 3-(1-isopropylpiperidin-4-yl)acrylate (6.87 g).

後処理

  1. temperaturecooling
  2. temperaturecooling, to the mixture
  3. stirringThe reaction solution is stirred for 3 hours
  4. extractionthe mixture is extracted with ethyl acetate
  5. washThe organic layer is washed with water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customto remove the solvent under reduced pressure
  9. customThe resulting residue is purified by NH-silica gel column chromatography (eluent: n-hexane/ethyl acetate=9/1)

出典と根拠

ORDレコード
ord-8f1065fd9fc54dbc8246f8d59beac4ef
出典データセット
uspto-grants-2009_05
特許番号
US07531537B2

反応ノート

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