Water → (5-Hydroxy-2-(4-hydroxyphenyl)-1-benzofuran-7-YL)acetonitrile

HRID 1835976Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of benzyl bromide 4 (0.0758 g, 0.238 mmole) in 5 mL dimethylformamide was added pulverized potassium cyanide (0.0232 g, 0.3563 mmole) and 18-crown-6 ether (0.100 g, 0.378 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 0.046 g (82%) of benzyl nitrile 5 as a yellow solid: Mp=128-130° C.; 1H NMR (DMSO-d6) δ 7.85 (d, 2 H, 8.7 Hz), 7.19 (s, 1 H), 7.06 (d, 2 H, J=8.7 Hz), 7.00 (d, 1 H, J=2.5 Hz), 6.88 (d, 1 H, J=2.1 Hz), 3.82 (s, 3 Hz), 3.79 (s, 3 H); MS, 285 (M+H)+

Workup

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

Sources & evidence

ORD record: ord-d4ecea4e5c32428c9debc19a45e81593
Source dataset: uspto-grants-2004_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06774248B2

Reaction notes

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