Diethylamine → HCID 86749181、化合物

HRID 2260879ノート

反応式

HRID 2260879 の反応式
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

参加物

10

反応物 4

HCID 8021DiethylamineHCID 2724141Tetrabutylammonium FluorideHCID 10964580HCID 10964580、化合物HCID 86749182HCID 86749182、化合物

生成物 1

HCID 86749181HCID 86749181、化合物収率 57%

試薬・触媒・溶媒 5

HCID 962Water触媒HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 241Benzene溶媒HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-20fa26698d5d4e7daf2fc51ec6de1e2f
出典データセット
uspto-grants-1995_12
特許番号
US05478959

反応ノート

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