Diethylamine → HCID 86749181, 화합물

HRID 2260879노트

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HRID 2260879 반응식
C[Si](C)(C)[C:3]#[C:4][C:5]#[C:6][CH3:7].CCCC[N+](CCCC)(CCCC)CCCC.[F-].[CH2:28]([S:35]/[C:36](/I)=[CH:37]\[CH:38]=[C:39](/[S:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)\[C:40]#[C:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.N(CC)CC>O.C1C=CC=CC=1.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.CN(C=O)C>[CH2:47]([S:46]/[C:39](=[CH:38]\[CH:37]=[C:36](/[S:35][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)\[C:3]#[C:4][C:5]#[C:6][CH3:7])/[C:40]#[C:41][Si:42]([CH3:45])([CH3:44])[CH3:43])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

참가 물질

10

반응물 4

HCID 8021DiethylamineHCID 2724141Tetrabutylammonium FluorideHCID 10964580HCID 10964580, 화합물HCID 86749182HCID 86749182, 화합물

생성물 1

HCID 86749181HCID 86749181, 화합물수율 57%

시약·촉매·용매 5

HCID 962Water촉매HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 241Benzene용매HCID 6228Dimethylformamide용매

실험 절차

To a DMF (5 mL) solution of 1-trimethylsilyl-1,3-pentadiyne (0.4 g, 2.94 mmol) under argon was added TBAF (0.8 g, 3 mmol) and several drops of water. The dark brown solution was stirred for 2 h at room temperature, then diluted with benzene (3 mL). The benzene layer was washed with saturated brine (5×5 mL). After drying (MgSO4) and filtering, the solution was transferred to a flask containing 8 (500 mg, 0.96 mmol), (Ph3P)2PdCl2 (34 mg, 0.048 mmol), CuI (9 mg, 0.048 mmol) and Et2NH (1 mL). The mixture was stirred under argon at room temperature for 40 h, and then concentrated in vacuo. Ether (100 mL) and water (25 mL) were added, the layers were separated, the ether layer was washed with brine (3×20 mL), dried (MgSO4), concentrated in vacuo and the residue purified by flash column chromatography (1:6 CH2Cl2 :hexanes) giving 9 as a yellow oil (0.25 g, 57% yield): 1H NMR δ 7.15-7.3 (m, 10 H), 6.99 (d, J=11.7 Hz, 1 H), 6.90 (d, J=11.7 Hz, 1 H), 4.09 (s, 2 H), 4.06 (s, 2 H), 1.98 (s, 3 H), 0.20 (s, 9 H); 13C NMR δ 120-138 (several), 102.32 102.09, 84.37, 80.86, 72.45, 64.35, 37.36, 37.27, 4.82, -0.200.

후처리

  1. washThe benzene layer was washed with saturated brine (5×5 mL)
  2. dry with materialAfter drying (MgSO4)
  3. filtrationfiltering
  4. customthe solution was transferred to a flask
  5. stirringThe mixture was stirred under argon at room temperature for 40 h
  6. concentrationconcentrated in vacuo
  7. additionEther (100 mL) and water (25 mL) were added
  8. customthe layers were separated
  9. washthe ether layer was washed with brine (3×20 mL)
  10. dry with materialdried (MgSO4)
  11. concentrationconcentrated in vacuo
  12. customthe residue purified by flash column chromatography (1:6 CH2Cl2 :hexanes)

출처 및 근거

ORD 기록
ord-20fa26698d5d4e7daf2fc51ec6de1e2f
출처 데이터셋
uspto-grants-1995_12
특허 번호
US05478959

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