Tetrabutylammonium Fluoride → tert-butyl 4-ethynyl-1H-pyrazole-1-carboxylate

HRID 2205852ノート

反応式

HRID 2205852 の反応式
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[N:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:11]=1)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:6]([C:7]1[CH:8]=[N:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:11]=1)#[CH:5]

参加物

4

反応物 2

HCID 2724141Tetrabutylammonium FluorideHCID 68478797tert-butyl 4-((trimethylsilyl)ethynyl)-1H-pyrazole-1-carboxylate

生成物 1

HCID 45382264tert-butyl 4-ethynyl-1H-pyrazole-1-carboxylate収率 62.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
2.5 °C

実験手順

tert-Butyl 4-((trimethylsilyl)ethynyl)-1H-pyrazole-1-carboxylate (3) (3.88 g 14.69 mmole) was dissolved in THF (40 mL) and cooled to 0-5° C. A 1M solution of tetra-n-butylammonium fluoride in THF (16 mL, 16 mmole) was added and the reaction was stirred for 20 minutes. The THF was evaporated and the residue was taken up in ethyl acetate (50 mL) and washed with water (×2) and with brine, then dried and evaporated. The residue was purified on a flash column (silica, eluting with 15% ethyl acetate in cyclohexane) to give the title compound (1.765 g, 62%). 1H-NMR (CDCl3, 500 MHz): δ 1.68 (s, 9H, 3.11 (s, 1H), 7.79 (s, 1H), 8.24 (s, 1H).

後処理

  1. customThe THF was evaporated
  2. washwashed with water (×2) and with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified on a flash column (silica, eluting with 15% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-6ac5a62d113843fd8ac31808ffce4cfe
出典データセット
uspto-grants-2016_06
特許番号
US09371319B2

反応ノート

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