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

HRID 2205852노트

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HRID 2205852 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

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온도
2.5 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-6ac5a62d113843fd8ac31808ffce4cfe
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371319B2

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