Potassium Carbonate → HCID 67272140, compound

HRID 250974Notes

Reaction equation

HRID 250974 reaction equation
[C:1]1([S:7]([C:9]2[C:10]([CH2:15][O:16]C(=O)C)=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[K+].[K+]>CO.C(Cl)Cl>[C:1]1([S:7]([C:9]2[C:10]([CH2:15][OH:16])=[N:11][CH:12]=[CH:13][CH:14]=2)=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 67272652HCID 67272652, compound

Product 1

HCID 67272140HCID 67272140, compoundYield 56.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the crude Acetic acid 3-benzenesulfinyl-pyridin-2-ylmethyl ester (268 mg) in anhydrous MeOH (4 mL) was added powdered K2CO3 (254 mg, 1.84 mmol) and the mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with CH2Cl2 (30 mL), filtered by vacuum filtration, and the filtrate was concentrated. Purification by flash chromatography on silica gel (Hexanes/EtOAc, 20:80 then 0:100) provided (3-Benzenesulfinyl-pyridin-2-yl)-methanol (128 mg, 42% over 2 steps) as a colorless oil. 1H NMR (CDCl3) δ 4.18 (t, 1H, J=5.7 Hz), 4.58 (dd, 1H, J=14.8, 4.3 Hz), 4.88 (dd, 1H, J=14.9, 5.3 Hz), 7.45-7.53 (m, 4H), 7.59-7.66 (m, 2H), 8.33 (dd, 1H, J=7.9, 1.4 Hz), 8.66 (dd, 1H, J=5.3, 1.8 Hz).

Workup

  1. filtrationfiltered by vacuum filtration
  2. concentrationthe filtrate was concentrated
  3. customPurification by flash chromatography on silica gel (Hexanes/EtOAc, 20:80

Sources & evidence

ORD record
ord-da4c809715a249549dc83437b0a43d14
Source dataset
uspto-grants-2011_01
Patent number
US07863293B2

Reaction notes

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