Acetic Anhydride → HCID 59138690, compound

HRID 1670725Notes

Reaction equation

HRID 1670725 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[C:25](OC(=O)C)(=[O:27])[CH3:26].C(=O)(O)[O-].[Na+]>CN(C)C1C=CN=CC=1.ClCCl.C(OCC)(=O)C.O>[C:25]([O:9][CH:8]([C:5]1[CH:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)(=[O:27])[CH3:26]

Participants

9

Reactant 4

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 20145726HCID 20145726, compound

Product 1

HCID 59138690HCID 59138690, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of (6-chloropyridin-3-yl)(phenyl)methanol (1.5 g, 6.8 mmol), diisopropylethylamine (2.5 mL, 15 mmol), 4-dimethylaminopyridine (86 mg, 0.7 mmol) in anhydrous dichloromethane (4 mL) was added acetic anhydride (1.4 mL, 15 mmol) dropwise at 0° C. under argon. After the reaction mixture was stirred at room temperature for 2 hours, water (1 mL) and then saturated aqueous sodium bicarbonate solution (20 mL) were added slowly to quench the reaction. The mixture was stirred at room temperature for 30 minutes and then extracted with dichloromethane (3×10 mL). The combined dichlormethane extracts were dried (Na2SO4) and concentrated. Silica gel flash chromatography (0-100% ethyl acetate in hexanes) gave (6-chloropyridin-3-yl)(phenyl)methyl acetate (1.7 g, 6.5 mmol, 96% yield) as a colorless liquid. MS found: (M+H)+=262.13.

Workup

  1. customto quench
  2. customthe reaction
  3. stirringThe mixture was stirred at room temperature for 30 minutes
  4. extractionextracted with dichloromethane (3×10 mL)
  5. dry with materialThe combined dichlormethane extracts were dried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-53cff92ac2884a0b9b0dc5a860357cb5
Source dataset
uspto-grants-2011_08
Patent number
US07994190B2

Reaction notes

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