Acetic Anhydride → HCID 59191232, compound

HRID 1023907Notes

Reaction equation

HRID 1023907 reaction equation
[F:1][C:2]1[N:7]=[C:6]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][OH:16])=[CH:11][C:10]=2[OH:17])[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[C:24](OC(=O)C)(=[O:26])[CH3:25]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:24]([O:16][CH2:15][C:12]1[CH:13]=[CH:14][C:9]([O:8][C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)=[C:10]([OH:17])[CH:11]=1)(=[O:26])[CH3:25]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 11430Potassium CarbonateHCID 59191287HCID 59191287, compound

Product 1

HCID 59191232HCID 59191232, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-[(6-fluoropyridin-2-yl)oxy]-5-(hydroxymethyl)phenol (0.42 mmol; 104 mg) under argon, in anhydrous DMF (0.8 mL), were added K2CO3 (0.5 mmol; 68 mg), DMAP (0.08 mmol; 12 mg), and acetic anhydride (0.41 mmol; 0.04 mL). The reaction was stirred at room temperature overnight. After dilution with ethyl acetate (4 mL), the organic phase was washed with saturated NaHCO3 (3*3 mL), dried (MgSO4), concentrated in vacuo, purified by preparative TLC (dichlorométhane) to yield the title compound as a clear oil (3 mg; 0.01 mmol; 3%).

Workup

  1. washAfter dilution with ethyl acetate (4 mL), the organic phase was washed with saturated NaHCO3 (3*3 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by preparative TLC (dichlorométhane)

Sources & evidence

ORD record
ord-e1a4fdf9a6424d44a2c6f76d482e4b94
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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