Tetrahydrofuran → HCID 86680608, compound

HRID 1497432Notes

Reaction equation

HRID 1497432 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]=[O:16])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1.C[Mg]Br.[CH2:20]1COC[CH2:21]1>C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:9]2[CH:10]=[CH:11][C:12]([CH:15]([OH:16])[CH2:20][CH3:21])=[N:13][CH:14]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 86680607HCID 86680607, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 86680608HCID 86680608, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-(3-methoxyphenyl)picolinaldehyde (0.75 g, 3.5 mmol), in THF (7 mL) was added methyl magnesium bromide (0.17 g, 8.8 mmol) under nitrogen at −40° C./ The reaction was brought to rt and then stirred at rt for 2 h. The contents were diluted with ethyl acetate (150 mL), quenched with ammonium chloride solution (100 mL), the organic layer washed with brine solution (2×100 mL), the layers separated, the organic layer was dried over sodium sulphate and distilled off to get the crude product. The compound was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane) to give 1-(5-(3-methoxyphenyl)pyridin-2-yl)propan-1-ol (450 mg, 53% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.73 (s, 1H), 8.04 (d, 1H), 7.52 (d, 1H), 7.38 (t, 1H), 7.26 (s, 1H), 7.23 (d, 1H), 6.95 (d, 1H), 5.28 (d, 1H), 4.54 (q, 1H), 3.81 (s, 3H), 1.7 (m, 1H), 1.8 (m, 1H), 0.86 (t, 3H); LC-MS m/z calcd for [M+H]+ 244.13. found 244.0.

Workup

  1. customwas brought to rt
  2. customquenched with ammonium chloride solution (100 mL)
  3. washthe organic layer washed with brine solution (2×100 mL)
  4. customthe layers separated
  5. dry with materialthe organic layer was dried over sodium sulphate
  6. distillationdistilled off
  7. customto get the crude product
  8. customThe compound was purified by flash chromatography (100-200 microns; 15% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bae7871344cb457ea627376a5850bddc
Source dataset
uspto-grants-2015_12
Patent number
US09199975B2

Reaction notes

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