Trimethylsilylacetylene → Methyl 4-ethynylbenzoate

HRID 527750

反応式

HRID 527750 の反応式
I[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.C[Si]([C:16]#[CH:17])(C)C>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[C:16]([C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1)#[CH:17]

参加物

6

反応物 2

HCID 66111TrimethylsilylacetyleneHCID 69273Methyl 4-iodobenzoate

生成物 1

HCID 640163Methyl 4-ethynylbenzoate収率 147.4%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418397HCID 178418397、化合物触媒HCID 1140Toluene溶媒

実験手順

To a solution of methyl 4-iodobenzoate (1.5 g, 5.72 mmol) and trimethylsilylacetylene (Aldrich, 1.58 mL, 11.45 mmol) in toluene (12 mL) were added Pd(PPh3)4 (0.66 g, 0.57 mmol), CuI (0.16 g, 0.86 mmol), and TEA (6.4 mL, 45.80 mmol). The resulting reaction mixture was purged with nitrogen for 3 min and stirred at rt for 3 h. The reaction mixture was diluted with ethyl acetate and NH4Cl solution. The organic layer was separated, washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 10% EtOAc/hexane) to afford the title compound as a white solid (1.35 g, 96%). 1H NMR (CDCl3) δ 7.98 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H), 3.92 (s, 3H), 0.27 (s, 9H); MS(ESI+) m/z 233.1 (M+H)+.

後処理

  1. customThe resulting reaction mixture
  2. customwas purged with nitrogen for 3 min
  3. additionThe reaction mixture was diluted with ethyl acetate and NH4Cl solution
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (eluting with 10% EtOAc/hexane)

出典と根拠

ORDレコード
ord-fd6cd99dcff044b0b717c51cc4dd5ec7
出典データセット
uspto-grants-2016_05
特許番号
US09345740B2

関連ノート

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