Hexane → HCID 9877656、化合物

HRID 2374206ノート

反応式

HRID 2374206 の反応式
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.[CH:9]1([C:15]#[CH:16])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1.CCCCCC>COCCOC.C(OCC)(=O)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>[CH:9]1([C:15]#[C:16][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=2)[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

参加物

7

反応物 3

HCID 8058HexaneHCID 70263EthynylcyclohexaneHCID 792052-Bromo-6-methylpyridine2 回

生成物 1

HCID 9877656HCID 9877656、化合物収率 77%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

2-Bromo-6-methyl pyridine (2.0 g, 11.6 mmol) and Cui (440 mg, 2.3 mmol) were combined in DME (30 mL), and argon gas was bubbled through the suspension for several minutes to deoxygenate the mixture. Triethylamne (8.0 mL, 58 mmol) and PdCl2(PPh3)2 (814 mg, 1.16 mmol) were added, followed by the dropwise addition of cyclohexylethyne (1.25 g, 11.6 mmol). The reaction was stirred at ambient temperature overnight. GC/MS showed no starting 2-bromo-6-methylpyridine remaining. The mixture was diluted with ethyl acetate (100 mL), and filtered through Celite.™, The pad was then thoroughly washed with ethyl acetate and the combined filtrates were washed with water (200 mL), brine (200 mL), dried over Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography eluting with hexane then 98:2, 96:4 hexane:ethyl acetate to afford 2-(cyclohexylethynyl)-6-me-thylpyridine (1.78 g, 77% yield) as a pale brown liquid that partially solidified on standing in the freezer. 1H NMR (CDCl3, 300 MHz) Δ7.52-7.46 (m, 1H), 7.20 (d, J=9 Hz, 1H), 7.03 (d, J=9 Hz, 1H), 2.6 (m, 1H), 2.54 (s, 3H), 2.93-2.89 (m, 2H), 1.78-1.73 (m, 2H), 1.57-1.54 (m, 3H), 1.36-1.32 (m, 3H). MS (ESI) 200.1 (M++H).

後処理

  1. customargon gas was bubbled through the suspension for several minutes
  2. customto deoxygenate the mixture
  3. filtrationfiltered through Celite
  4. wash™, The pad was then thoroughly washed with ethyl acetate
  5. washthe combined filtrates were washed with water (200 mL), brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate was concentrated in vacuo
  9. customthe residue was purified by column chromatography
  10. washeluting with hexane

出典と根拠

ORDレコード
ord-33c66a2f1bfa4851abbe0f570252bb09
出典データセット
uspto-grants-2008_12
特許番号
US07462619B2

反応ノート

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