Ammonium Chloride → 1-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol

HRID 2075273Notes

Reaction equation

HRID 2075273 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]=[O:21])=[CH:18][C:17]=3[F:24])=[CH:13][C:12]=2[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:26][Mg]Br.[NH4+].[Cl-]>C1COCC1>[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]2[O:15][C:14]([C:16]3[CH:23]=[CH:22][C:19]([CH:20]([OH:21])[CH3:26])=[CH:18][C:17]=3[F:24])=[CH:13][C:12]=2[CH:25]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59595923HCID 59595923, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 584152741-(4-(5-Benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a mixture of 4-(5-benzylbenzofuran-2-yl)-3-fluorobenzaldehyde (0.559 g, 2 mmol) in THF at 0° C. was added methyl-magnesium bromide (1.4M solution in toluene/THF=3:1, 2.40 mL, 3 mmol) dropwise over 5 min. The mixture was allowed to stir for 20 min at 0° C., treated with NH4Cl, extracted with EtOAc, dried over MgSO4, and evaporated. The crude product was purified by flash chromatography (EtOAc/hexanes) to give 1-(4-(5-benzylbenzofuran-2-yl)-3-fluorophenyl)ethanol. 1H NMR (300 MHz, CDCl3) δ ppm 7.98 (t, J=8.0 Hz, 1H), 7.38-7.46 (m, 2H), 7.10-7.34 (m, 9H), 4.77-5.04 (m, 1H), 4.08 (s, 2H), 1.85 (d, J=3.8 Hz, 1H), 1.46-1.60 (m, 3H). MS (ESI) m/z: Calculated; 346.1 Observed: 347.1 (M++1).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialdried over MgSO4
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (EtOAc/hexanes)

Sources & evidence

ORD record
ord-0ae36410dec842bda17751b6ac514b6b
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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