Diethyl Ether → Benzofuran-5-yl(phenyl)methanol

HRID 2075191

Reaction equation

HRID 2075191 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418255HCID 178418255, compound

Product 1

HCID 58415371Benzofuran-5-yl(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-benzofuran-5-carbaldehyde (2.70 g, 18.5 mmol) in 50 mL THF under N2 was added phenylmagnesium bromide 3.0M solution in diethyl ether (7.39 mL, 22.2 mmol). The reaction was allowed to stir for 1 h, then was quenched with NH4Cl sat'd aq., extracted with diethyl ether, washed with brine, dried over anhyd. sodium sulfate, filtered, and concentrated in vacuo to a solid to give benzofuran-5-yl(phenyl)methanol which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94 (d, J=2.0 Hz, 1H), δ 7.64 (s, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.36-7.42 (m, 2H), 7.26-7.33 (m, 3H), 7.19 (t, J=7.3 Hz, 1H), 6.92 (d, J=1.5 Hz, 1H), 5.88 (d, J=4.0 Hz, 1H), 5.77-5.83 (m, 1H).

Workup

  1. customwas quenched with NH4Cl sat'd aq.
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. customdried over anhyd
  5. filtrationsodium sulfate, filtered
  6. concentrationconcentrated in vacuo to a solid

Sources & evidence

ORD record
ord-2bb8768110694cde84453063495b7b0f
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Linked notes

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