Hydrochloric Acid → 2-Ethynyl-6-methylpyridine

HRID 8214

反応式

HRID 8214 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C[Si]([C:13]#[CH:14])(C)C.[OH-].[Na+].Cl>C(N(CC)CC)C.CO.[Cu]I.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>[C:13]([C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1)#[CH:14]

参加物

9

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 66111TrimethylsilylacetyleneHCID 792052-Bromo-6-methylpyridine

生成物 1

HCID 134006352-Ethynyl-6-methylpyridine収率 341.4%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 887Methanol溶媒HCID 8471Triethylamine溶媒

実験手順

A solution of 2-bromo-6-methylpyridine (0.5 g, 2.9 mmol) and (trimethylsilyl)acetylene (0.29 g, 2.9 mmol) in triethylamine (15 mL) is purged with argon. Copper(I) iodide (11 mg, 0.06 mmol) and (PPh3)2PdCl2 (42 mg, 0.06 mmol) are added and the reaction is stirred under argon at room temperature for 2 h. The solvent is removed in vacuo and the residue is diluted in ethyl acetate (50 mL) and water (50 mL). The organic is separated and washed with brine. The solvent is removed to afford a dark oil. This oil is diluted in methanol (50 mL) and treated with a 1 N sodium hydroxide solution (10 mL) and stirred for 3 h at room temperature. The aqueous is neutralized with 1 N hydrochloric acid and extracted with ethyl acetate. The solvent is removed in vacuo to afford a dark oil that is purified by SiO2 column chromatography to yield 1.16 g (24%) of the title compound as a light yellow oil.

後処理

  1. customThe solvent is removed in vacuo
  2. additionthe residue is diluted in ethyl acetate (50 mL)
  3. customThe organic is separated
  4. washwashed with brine
  5. customThe solvent is removed
  6. customto afford a dark oil
  7. stirringstirred for 3 h at room temperature
  8. extractionextracted with ethyl acetate
  9. customThe solvent is removed in vacuo
  10. customto afford a dark oil that
  11. customis purified by SiO2 column chromatography

出典と根拠

ORDレコード
ord-24f8476f7c90486db479cc7ee0b431c1
出典データセット
uspto-grants-2006_08
特許番号
US07087626B2

関連ノート

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