Water → HCID 10308348, compound

HRID 1835981Notes

Reaction equation

HRID 1835981 reaction equation
Br[CH2:2][C:3]1[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=[C:5]([O:20][CH3:21])[CH:4]=1.[C-:22]#[N:23].[K+].C1OCCOCCOCCOCCOCCOC1.O>CN(C)C=O>[CH3:21][O:20][C:5]1[CH:4]=[C:3]([CH2:2][C:22]#[N:23])[C:11]2[O:10][C:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)=[CH:8][C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 9032Potassium CyanideHCID 2855718-Crown-6HCID 102867967-Bromomethyl-5-methoxy-2-(4-methoxy-phenyl)-benzofuran

Product 1

HCID 10308348HCID 10308348, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl bromide 17 (0.640 g, 1.843 mmole) in 100 mL dimethylformamide was added pulverized potassium cyanide (0.186 g, 2.76 mmole) and 18-crown-6 ether (0.786 g, 2.965 mmole). After stirring at 80° C. for 2 hours, the reaction mixture was cooled and poured into water and extracted with ethyl acetate. The combined organic phases were washed with saturated sodium bicarbonate, water, brine, and dried with magnesium sulfate. The organic phases were concentrated and the residue was loaded on to silica gel and chromatographed with silica gel (hexanes:ethyl acetate, 9:1) to afford 0.529 g (98%) of acetonitrile 18 as a white solid: Mp=149-150° C.; 1H NMR (DMSO-d6) δ 7.87 (d, 2 H, J=8.8 Hz), 7.26 (s, 1 H), 7.12 (d, 1 H, J=2.4 Hz),), 7.10 (d, 2 H, J=8.7 Hz), 6.88 (d, 1 H, J=2.4 Hz), 4.42 (s, 2 H), 3.82 (s, 3 H), 3.81 (s, 3 H); MS 294 (M+H)+

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  4. dry with materialdried with magnesium sulfate
  5. concentrationThe organic phases were concentrated
  6. customchromatographed with silica gel (hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-491e8b496ea34a08a8534a894347f9c5
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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