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tert-butyl 2-cyano-2-(1-methyl-1H-pyrazol-5-yl)acetate → 2-(1-methyl-1H-pyrazol-5-yl)acetonitrile

HRID 931132
Notes
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Reaction equation

HRID 931132 reaction equation
[C:1]([CH:3]([C:11]1[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=1)C(OC(C)(C)C)=O)#[N:2]>FC(F)(F)C(O)C(F)(F)F.C(OCC)C>[CH3:16][N:15]1[C:11]([CH2:3][C:1]#[N:2])=[CH:12][CH:13]=[N:14]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 1

HCID 117966348tert-butyl 2-cyano-2-(1-methyl-1H-pyrazol-5-yl)acetate

Product 1

HCID 252483742-(1-methyl-1H-pyrazol-5-yl)acetonitrileYield 95.9%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Procedure

A mixture of tert-butyl 2-cyano-2-(1-methyl-1H-pyrazol-5-yl)acetate (130 mg, 0.588 mmol) in hexafluoroisopropanol (1 mL) was submitted to microwave radiation at 130° C. for 15 minutes. The reaction mixture was diluted with diethyl ether (30 mL), washed with water (5 mL) and brine (5 mL), dried over magnesium sulfate, filtered, concentrated under reduced pressure and dried under high vacuum to afford 2-(1-methyl-1H-pyrazol-5-yl)acetonitrile (68.3 mg) as a pale yellow oil. 1H NMR (500 MHz, CDCl3) δ 3.77 (s, 2H), 3.89 (s, 3H), 6.30 (s, 1H), 7.45 (s, 1H).

Workup

  1. customat 130° C.
  2. customfor 15 minutes
  3. washwashed with water (5 mL) and brine (5 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-8fca63e6286b461b813c8aaf08cf8713
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296745B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes