Diethyl Ether → 1-(Benzofuran-5-yl)-1-phenylethanol

HRID 2075193Notes

Reaction equation

HRID 2075193 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:18][Mg]Br.C(OCC)C>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)([OH:11])[CH3:18])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 58415352Benzofuran-5-yl(phenyl)methanoneHCID 178418573HCID 178418573, compound

Product 1

HCID 584152691-(Benzofuran-5-yl)-1-phenylethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of benzofuran-5-yl(phenyl)methanone (1.0 g, 4.5 mmol) in 20 mL THF under nitrogen at 0° C. was added methylmagnesium bromide 3.0M in diethyl ether (2.2 mL, 6.7 mmol) dropwise via syringe. The reaction was allowed to warm to ambient temperature slowly. The reaction was quenched with sat'd aq. NH4Cl and DCM. The aqueous layer was extracted 2×DCM, and the combined organics were dried over anhyd sodium sulfate, filtered, and concentrated in vacuo to give 1-(benzofuran-5-yl)-1-phenylethanol as an oil, which was used without further purification. MS (ESI) m/z: Calculated: 238.1; Observed: 238.8 (M++1).

Workup

  1. customThe reaction was quenched with sat'd aq. NH4Cl and DCM
  2. extractionThe aqueous layer was extracted 2×DCM
  3. dry with materialthe combined organics were dried over anhyd sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8fa88431a8d3486fb78d60917df48d64
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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