Tetrabutylammonium Fluoride → 1-(3-Ethynylphenyl)cyclopropanecarboxamide

HRID 592457Notes

Reaction equation

HRID 592457 reaction equation
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]

Participants

6

Reactant 2

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

Product 1

HCID 867123321-(3-Ethynylphenyl)cyclopropanecarboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-afe7c58327ec47a089f563d722cccedb
Source dataset
uspto-grants-2016_01
Patent number
US09238644B2

Reaction notes

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