Methyl 4-trimethylsilylethynylbenzoate → Methyl 4-ethynylbenzoate

HRID 527751

反応式

HRID 527751 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:6]([C:7]1[CH:16]=[CH:15][C:10]([C:11]([O:13][CH3:14])=[O:12])=[CH:9][CH:8]=1)#[CH:5]

参加物

4

反応物 2

HCID 640161Methyl 4-trimethylsilylethynylbenzoateHCID 2724141Tetrabutylammonium Fluoride

生成物 1

HCID 640163Methyl 4-ethynylbenzoate収率 76%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of methyl 4-((trimethylsilyl)ethynyl)benzoate (1.35 g, 5.35 mmol) in THF (10 mL) was added TBAF (1 M solution in THF, 10.7 mL, 10.70 mmol). The resulting brown reaction mixture was stirred at rt for 3 h and concentrated in vacuo. The residue was purified by flash column chromatography (eluting with 5% EtOAc/hexane) to afford the title compound as a white solid (0.65 g, 76%). 1H NMR (CDCl3) δ 8.00 (d, J=8.6 Hz, 2H), 7.56 (d, J=8.6 Hz, 2H), 3.93 (s, 3H), 3.23 (s, 1H).

後処理

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by flash column chromatography (eluting with 5% EtOAc/hexane)

出典と根拠

ORDレコード
ord-47111b569f9f4343b680312b67ded67b
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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