Water → HCID 86638786, compound

HRID 1689597Notes

Reaction equation

HRID 1689597 reaction equation
[F-].[K+].[C:3]([C:5]([C:27]#[N:28])=[C:6]1[C:10]([C:11]#[N:12])=[C:9]([C:13]2[CH:18]=[CH:17][C:16]([C:19]#[C:20][Si](C)(C)C)=[CH:15][CH:14]=2)[C:8]([CH3:26])([CH3:25])[O:7]1)#[N:4].O>C1COCC1.CO>[C:11]([C:10]1[C:6](=[C:5]([C:3]#[N:4])[C:27]#[N:28])[O:7][C:8]([CH3:26])([CH3:25])[C:9]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][CH:14]=1)#[N:12]

Participants

5

Reactant 3

HCID 962WaterHCID 522689Potassium FluorideHCID 86638787HCID 86638787, compound

Product 1

HCID 86638786HCID 86638786, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

(RS01039) Potassium fluoride (260 mg, 4.5 mmol) was added to a solution of 2-dicyanomethylene-3-cyano-5,5-dimethyl-4-(4′-trimethylsilylethynylphenyl)-2,5-dihydrofuran (500 mg, 1.4 mmol) in degassed THF/methanol (1.5:1, 40 mL). The reaction mixture was stirred for 24 h at room temperature, poured into water, stirred for 1 hr, kept in the refrigerator overnight, filtered and air-dried. The product was recrystallized from dichloromethane/1-propanol. Yield: 330 mg. (90%). mp: 225° C. 1H NMR (400 MHz, CDCl3) δ 7.72 (d, J=8.8 Hz, 2H), 7.67 (d, J=8.8 Hz, 2H), 3.36 (s, 1H), 1.81 (s, 6H). 13C NMR (100 MHz, CDCl3) δ 176.24, 174.31, 133.32, 128.00, 126.93, 110.98, 110.06, 109.97, 102.50, 99.08, 82.29, 81.71, 26.13. IR (neat, cm−1 2965, 2226, 1623, 1614, 1534.

Workup

  1. stirringstirred for 1 hr
  2. customkept in the refrigerator overnight
  3. filtrationfiltered
  4. customair-dried
  5. customThe product was recrystallized from dichloromethane/1-propanol

Sources & evidence

ORD record
ord-b8e963ab3e0742c4a5a28ef554bb8465
Source dataset
uspto-grants-2012_04
Patent number
US08153446B2

Reaction notes

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