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Potassium Cyanide → 2-m-Tolyltetrahydrofuran-2-carbonitrile

HRID 1620992
Notes
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Reaction equation

HRID 1620992 reaction equation
Cl[CH2:2][CH2:3][CH2:4][C:5]([C:7]1[CH:8]=[C:9]([CH3:13])[CH:10]=[CH:11][CH:12]=1)=[O:6].[C-:14]#[N:15].[K+]>CO.C(OCC)(=O)C>[C:9]1([CH3:13])[CH:10]=[CH:11][CH:12]=[C:7]([C:5]2([C:14]#[N:15])[CH2:4][CH2:3][CH2:2][O:6]2)[CH:8]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 215346004-Chloro-1-(m-tolyl)butan-1-one

Product 1

HCID 895247412-m-Tolyltetrahydrofuran-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
35 °C

Procedure

To a solution of Example 91B (1.56 g, 8 mmol) in MeOH (15 mL) was carefully added KCN (0.8 g, 12.3 mmol) and the mixture was warmed at 35° C. for 48 hours. The mixture was diluted with 50 mL ethyl acetate, washed with conccentrated aqueous NaHCO3 (20 mL) and brine (10 mL). The aqueous solution was oxidized with excessive NaC100. The organic phase was dried over MgSO4, filtered, and concentrated to give the title compound as an oil which was used directly for the next step (1.35 g, 90%). LC-MS: m/z (M+H): 161.

Workup

  1. washwashed with conccentrated aqueous NaHCO3 (20 mL) and brine (10 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-80c75ee2584e49bdaf51226baae5d2fb
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772500B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes