Pyridine → HCID 59443558, compound

HRID 1927645Notes

Reaction equation

HRID 1927645 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O-:19])=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)O[C:37](=O)[C:36]2[CH:35]=[CH:34][CH:33]=[CH:32][C:31]1=2)=O>ClCCl>[O:1]=[CH:2][CH2:3][CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[C:12]([C:17]([O:19][CH2:37][C:36]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[O:18])=[N:13][CH:14]=[CH:15][CH:16]=2)=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 86644170HCID 86644170, compound

Product 1

HCID 59443558HCID 59443558, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 3-[4-(3-hydroxypropyl)phenyl]pyridine-2-carboxylate (245 mg, 0.704 mmol) in dichloromethane (3 ml) and pyridine (357 uL, 3.52 mmol) was added a solution of Dess-Martin periodinane (358 mg, 0.845 mmol) in dichloromethane (3 mL). After stirring at rt for 30 min, the reaction was quenched by addition of a mixture of 15% Na2S2O3 (2 mL) and saturated NaHCO3 (3 mL). The organic layer was separated and the aqueous layer was extracted by ethyl acetate (3×). The combined extracts were washed with water and brine, dried over MgSO4, filtered and concentrated, and the residue was purified by flash column chromatography on silica gel eluting 10-50% ethyl acetate in hexanes) to afford the title compound. LC-MS: m/e 346 (M+H)+. 1HNMR (CDCl3, 500 MHz): δ 9.86 (1H, t, J=1.5 Hz), 8.68 (1H, dd, J=4.5, 1.7 Hz), 7.76 (1H, dd, J=8.0, 1.7 Hz), 7.48 (1H, dd, J=8.0, 4.5 Hz), 7.30 (3H, m), 7.26 (2H, d, J=8.0 Hz), 7.19 (2H, d, J=8.0 Hz), 7.14 (2H, dd, J=7.5, 2.0 Hz), 5.22 (2H, s), 3.00 (2H, t, J=7.5 Hz), 2.82 (2H, t, 7.5 Hz).

Workup

  1. customthe reaction was quenched by addition of a mixture of 15% Na2S2O3 (2 mL) and saturated NaHCO3 (3 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted by ethyl acetate (3×)
  4. washThe combined extracts were washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe residue was purified by flash column chromatography on silica gel eluting 10-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f80850f9a5834d56810dc4bfc32dab49
Source dataset
uspto-grants-2012_05
Patent number
US08183275B2

Reaction notes

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