3-Phenylbenzo[b]thiophene-2-carbaldehyde → 1-(3-Phenylbenzo[b]thiophen-2-yl)ethanol

HRID 242880Notes

Reaction equation

HRID 242880 reaction equation
[C:1]1([C:7]2[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[S:10][C:11]=2[CH:12]=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:18][Mg]Br>C1COCC1.C(OCC)C>[C:1]1([C:7]2[C:8]3[CH:17]=[CH:16][CH:15]=[CH:14][C:9]=3[S:10][C:11]=2[CH:12]([OH:13])[CH3:18])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 105141003-Phenylbenzo[b]thiophene-2-carbaldehydeHCID 178418573HCID 178418573, compound

Product 1

HCID 584591571-(3-Phenylbenzo[b]thiophen-2-yl)ethanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-phenylbenzo[b]thiophene-2-carbaldehyde (430 mg, 1.87 mmol) in THF (10 mL) at −78° C. and under a nitrogen atmosphere was added 3.0M methylmagnesium bromide in diethyl ether (1.24 mL) and stirring continued for 30 min. The reaction mixture was quenched with a saturated solution of NH4Cl (20 mL) and slowly warmed to RT. The mixture was extracted with EtOAc (×2) and the combined organic fractions washed with water, dried (Na2SO4) and concentrated in vacuo affording the title compound as a white solid (472 mg, quantitative). 1H NMR (CDCl3, 400 MHz): δ 7.88-7.84 (1H, m), 7.52-7.28 (8H, m), 5.21 (1H, q, J=6.35 Hz), 2.03 (1H, s), 1.59 (3H, d, J=6.63 Hz)

Workup

  1. customThe reaction mixture was quenched with a saturated solution of NH4Cl (20 mL)
  2. extractionThe mixture was extracted with EtOAc (×2)
  3. washthe combined organic fractions washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-756d7bcc097a4add8818887be8179989
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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