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Hydrochloric Acid → 7,8-Difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-ol

HRID 2244842
ノート
印刷プレビュー

反応式

HRID 2244842 の反応式
[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4](I)[C:3]=1[OH:19].[C:20]([CH:22]1[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]1)#[CH:21].Cl>C(N(CC)CC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[F:1][C:2]1[C:11]([F:12])=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[O:9]2)=[C:4]([C:21]#[C:20][CH:22]2[CH2:27][CH2:26][CH:25]([CH2:28][CH2:29][CH3:30])[CH2:24][CH2:23]2)[C:3]=1[OH:19]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 313Hydrochloric AcidHCID 218706261-Ethynyl-4-propylcyclohexaneHCID 592152577,8-Difluoro-5-iodo-2-pentylchroman-6-ol

生成物 1

HCID 592152687,8-Difluoro-2-pentyl-5-(4-propylcyclohexylethynyl)chroman-6-ol

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒
HCID 178418476
HCID 178418476、化合物
触媒
HCID 8471Triethylamine溶媒

実験手順

8.0 g (20.9 mmol) of 7,8-difluoro-5-iodo-2-pentylchroman-6-ol are stirred at 50° C. for 19 h together with 4.72 g (31.4 mmol) of 1-ethynyl-4-propylcyclohexane in the presence of 441 mg (0.63 mmol) of bis(triphenylphosphine)palladium(II) chloride and 120 mg (0.63 mmol) of copper(I) iodide in 90 ml of triethylamine. After cooling, the batch is added to ice/water and acidified using hydrochloric acid. The mixture is extracted a number of times with MTBE, and the combined extracts are washed with water and sat. sodium chloride soln. The solution is dried using sodium sulfate and concentrated to dryness. The residue is purified by column chromatography (SiO2, 1-chlorobutane). The phenol obtained is used directly for the following reaction.

後処理

  1. temperatureAfter cooling
  2. extractionThe mixture is extracted a number of times with MTBE
  3. washthe combined extracts are washed with water and sat. sodium chloride soln
  4. customThe solution is dried
  5. concentrationconcentrated to dryness
  6. customThe residue is purified by column chromatography (SiO2, 1-chlorobutane)

出典と根拠

ORDレコード
ord-3d18bb44540243279dc087295fe9109e
出典データセット
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07678929B2

反応ノート

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