Ethanol → 7-Ethoxymethyl-2-(4-hydroxy-phenyl)-benzofuran-5-ol

HRID 1835977Notes

Reaction equation

HRID 1835977 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.[OH-].[K+].[CH2:22]([OH:24])[CH3:23]>>[CH2:22]([O:24][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)[CH3:23]

Participants

4

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 10171939HCID 10171939, compound

Product 1

HCID 102363797-Ethoxymethyl-2-(4-hydroxy-phenyl)-benzofuran-5-olYield 51%

Procedure

To a solution of benzyl bromide 4 (0.05 g, 0.159 mmole) in 5 mL ethanol was added potassium hydroxide (0.350 g, 0.627 mmole). After stirring at R.T. for 1 hour, the solvent was evaporated and the residue was 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 on silica gel (hexanes:ethyl acetate, 9:1) to afford 0.039 g (51%) of ethyl ether 7 as a tan solid: Mp=166-168° C.; 1H NMR (DMSO-d6) δ 9.82 (br s, 1 H), 9.12 (bs, 1 H), 7.70 (d, 2 H, J=8.6 Hz), 7.02 (s, 1 H), 6.86 (d, 2 H, J=8.6 Hz), 6.81 (d, 1 H, J=2.1 Hz), 6.69 (d, 1 H, J=2.2 Hz), 4.71 (s, 2 H), 3.56 (q, 2 H, J=7.2 Hz), 1.18 (t, 3 H, J=7.2 Hz); MS 283 (M−H)−

Workup

  1. customthe solvent was evaporated
  2. additionthe residue was poured into water
  3. extractionextracted with ethyl acetate
  4. washThe combined organic phases were washed with saturated sodium bicarbonate, water, brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationThe organic phases were concentrated
  7. customchromatographed on silica gel (hexanes:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-b26f9210be074795a99e235dc0b555ad
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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