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Tetrabutylammonium Fluoride → 1-(3-Ethynylphenyl)cyclopropanecarboxamide

HRID 592457
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HRID 592457 반응식
CCCC[N+](CCCC)(CCCC)CCCC.[F-].C([Si]([C:29]#[C:30][C:31]1[CH:32]=[C:33]([C:37]2([C:40]([NH2:42])=[O:41])[CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1)(C(C)C)C(C)C)(C)C>C1COCC1.O.CCOC(C)=O>[C:30]([C:31]1[CH:32]=[C:33]([C:37]2([C:40]([NH2:42])=[O:41])[CH2:39][CH2:38]2)[CH:34]=[CH:35][CH:36]=1)#[CH:29]
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참가 물질

6

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 867123331-(3-((Triisopropylsilyl)ethynyl)phenyl)cyclopropanecarboxamide

생성물 1

HCID 867123321-(3-Ethynylphenyl)cyclopropanecarboxamide

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857
Ethyl Acetate
용매

실험 절차

A 1.0 M TBAF solution in THF (10.5 mL, 10.5 mmol) was added to a solution of 1-(3-((triisopropylsilyl)ethynyl)phenyl)cyclopropanecarboxamide A59 (1.20 g, 3.50 mmol) in THF (50 mL) and stirred for 15 minutes. The mixture was diluted with water (200 mL) and EtOAc (200 mL) before the organic fraction was separated and washed with 0.5 M citric acid solution (200 mL), water (200 mL), brine (50 mL) and dried (Na2SO4). The volatiles were removed in vacuo and the resulting solid was suspended in cyclohexane (50 mL) and sonicated for 10 minutes. The solid was collected by filtration and dried to give the title compound A60 as a tan solid (386 mg, 59%). LCMS-A: rt 5.635 min; m/z 186.2 [M+H]+.

후처리

  1. customwas separated
  2. washwashed with 0.5 M citric acid solution (200 mL), water (200 mL), brine (50 mL)
  3. dry with materialdried (Na2SO4)
  4. customThe volatiles were removed in vacuo
  5. customsonicated for 10 minutes
  6. filtrationThe solid was collected by filtration
  7. customdried

출처 및 근거

ORD 기록
ord-afe7c58327ec47a089f563d722cccedb
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09238644B2

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