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

HRID 1620992Notes

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

Participants

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

washwashed with conccentrated aqueous NaHCO3 (20 mL) and brine (10 mL)
dry with materialThe organic phase was dried over MgSO4
filtrationfiltered
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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