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Water → Methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

HRID 402295
ノート
印刷プレビュー

反応式

HRID 402295 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=2[CH:20]=1.[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:34]=[CH:33][C:32](OB(O)O)=[CH:31][CH:30]=1)[CH2:22][CH2:23]C.C(=O)([O-])[O-].[K+].[K+].O>C1(C)C(CCO)=CC=CC=1.O>[CH2:21]([O:25][CH2:26][CH2:27][O:28][C:29]1[CH:30]=[CH:31][C:32]([C:2]2[CH:3]=[CH:4][C:5]3[N:12]([CH2:13][CH2:14][CH3:15])[CH2:11][CH2:10][CH2:9][C:8]([C:16]([O:18][CH3:19])=[O:17])=[CH:7][C:6]=3[CH:20]=2)=[CH:33][CH:34]=1)[CH2:22][CH3:23]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 230910874-(2-Butoxyethoxy)phenylboric acidHCID 68650111Methyl 8-bromo-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate

生成物 1

HCID 68650188Methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate収率 56.7%

試薬・触媒・溶媒 1

HCID 66602552Toluene-ethanol water溶媒

実験手順

Under argon atmosphere, a mixture of methyl 8-bromo-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate (1.5 g), 4-(2-butoxyethoxy)phenyl boric acid (1.29 g) and potassium carbonate (1.23 g) in toluene-ethanol-water (45-4.5-4.5 ml) was stirred at room temperature for 1 hour. To the reaction system was added tetrakis-(triphenylphosphine)palladium (0.26 g) was added, and the mixture was refluxed for 4 hours. After cooling to room temperature, water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried with magnesium sulfate. After concentration under reduced pressure, the residue was separated to purify by column chromatography (ethyl acetate:hexane=1:49→1:19→1:9) to give methyl 8-[4-(2-propoxyethoxy)phenyl]-1-propyl-1,2,3,4-tetrahydro-1-benzazocine-5-carboxylate (1.10 g) as a yellow oily material.

後処理

  1. additionwas added
  2. temperaturethe mixture was refluxed for 4 hours
  3. temperatureAfter cooling to room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated brine
  6. dry with materialdried with magnesium sulfate
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue was separated
  9. customto purify by column chromatography (ethyl acetate:hexane=1:49→1:19→1:9)

出典と根拠

ORDレコード
ord-6b60f0d914fd4f1f9b07b8c9f4c935e5
出典データセット
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08741943B2

反応ノート

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