Hexane → HCID 9877656, 화합물

HRID 902088노트

반응식

HRID 902088 반응식
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

참가 물질

7

반응물 3

HCID 8058HexaneHCID 70263EthynylcyclohexaneHCID 792052-Bromo-6-methylpyridine2회

생성물 1

HCID 9877656HCID 9877656, 화합물수율 77%

시약·촉매·용매 3

HCID 178418476HCID 178418476, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-97c83db0fca44fcc8649f8cfe8885e51
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07365074B2

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