Hydrochloric Acid → 3-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate

HRID 324766

反応式

HRID 324766 の反応式
[N:1]1([CH2:7][CH2:8][OH:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].Cl[CH2:13][C:14](=[O:28])[CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17].Cl>C1COCC1>[N:1]1([CH2:7][CH2:8][O:9][CH2:13][C:14](=[O:28])[CH2:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:17])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 18232N-PiperidinoethanolHCID 24758Sodium hydrideHCID 220055463-Phenylpropyl 4-chloroacetoacetate

生成物 1

HCID 220055123-Phenylpropyl 4-(2-(1-piperidinyl)ethoxy)acetoacetate収率 67.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

2-(1-Piperidinyl)ethanol (15 mL, 113 mmol) in THF (50 mL) was added dropwise to a suspension of sodium hydride (7 g, 175 mmol) in THF (200 mL) at 0° C. The mixture was then stirred for 1 h at room temperature, cooled to 0° C., 3-phenylpropyl 4-chloroacetoacetate (22 mL, 103 mmol) in THF (50 mL) was added dropwise and the reaction mixture was then stirred for 18 h whilst warming to room temperature. 1N Hydrochloric acid was added until the mixture was acidic and the aqueous layer was then separated. The organic layer was extracted twice more with 1N hydrochloric acid. The combined acid layers were made basic to pH 8 with sodium hydrogen carbonate and extracted with chloroform. The combined extracts were washed with brine, dried and evaporated to give the title compound (24 g) as an oil. Electrospray MS m/z 348 [M+H]+.

後処理

  1. temperaturecooled to 0° C.
  2. stirringthe reaction mixture was then stirred for 18 h
  3. temperaturewhilst warming to room temperature
  4. customthe aqueous layer was then separated
  5. extractionThe organic layer was extracted twice more with 1N hydrochloric acid
  6. extractionextracted with chloroform
  7. washThe combined extracts were washed with brine
  8. customdried
  9. customevaporated

出典と根拠

ORDレコード
ord-a9f7ca5fb7cf4d46a7a423dcaa90353b
出典データセット
uspto-grants-2001_04
特許番号
US06218538B1

関連ノート

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