Acrylonitrile → 6-Trifluoromethoxy-2H-chromene-3-carbonitrile

HRID 1697457

Reaction equation

HRID 1697457 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([O:10][C:11]([F:14])([F:13])[F:12])=[CH:6][C:3]=1[CH:4]=O.[C:15](#[N:18])[CH:16]=[CH2:17].C1N2CCN(CC2)C1>CCOCC>[F:12][C:11]([F:14])([F:13])[O:10][C:7]1[CH:6]=[C:3]2[C:2](=[CH:9][CH:8]=1)[O:1][CH2:17][C:16]([C:15]#[N:18])=[CH:4]2

Participants

5

Reactant 3

HCID 7855AcrylonitrileHCID 9237DabcoHCID 12680582-Hydroxy-5-(trifluoromethoxy)benzaldehyde

Product 1

HCID 669452446-Trifluoromethoxy-2H-chromene-3-carbonitrileYield 49.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
130 °C

Procedure

To a microwave tube was added 2-hydroxy-5-trifluoromethoxybenzaldehyde (1 g, 5.0 mmol), 2-propenenitrile (1.6 mL, 24.3 mmol) and triethylenediamine (136 mg, 1.2 mmol). The reaction was heated in the microwave at 130° C. for 1 hour. After cooling, the resulting solution was diluted with ether (100 mL) and washed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL), dried (MgSO4), filtered and concentrated. Flash chromatography (0 to 15% EtOAc in hexanes over 1 hour) gave the product (600 mg) as a solid. m/z=242.4 (M+1), r.t.=3.72 mins. 1H NMR (400 MHz; CDCl3) δ 7.14-7.12 (2H, m), 7.00 (1H, s), 6.89 (1H, d), 4.85 (2H, s).

Workup

  1. temperatureAfter cooling
  2. washwashed with 1N NaOH (50 mL), 1N HCl (50 mL) and brine (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-9b24365928e2465c918785947e07515b
Source dataset
uspto-grants-2012_04
Patent number
US08163901B2

Linked notes

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