Potassium Carbonate → HCID 69489153, compound

HRID 851970Notes

Reaction equation

HRID 851970 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[C:7]([F:12])[CH:6]=1)[CH3:2].Cl[CH2:15][CH2:16][N:17]1[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:13])[C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[C:7]([F:12])[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 13745619Ethyl 3-fluoro-4-hydroxybenzoate

Product 1

HCID 69489153HCID 69489153, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

3-Fluoro-4-hydroxybenzoic acid ethyl ester (0.20 g, 1.1 mmol) and N-(2-chloroethyl)morpholine (0.22 g, 1.2 mmol) were dissolved in dry DMF (10 ml). Potassium carbonate (1.88 g, 5 mmol) was added and the turbid reaction mixture was stirred overnight at 40° C. under an argon atmosphere. The reaction mixture was concentrated under reduced pressure and ethyl acetate was added to the residue followed by washing with NaHCO3 (½ sat., 3×), water, brine, dried (MgSO4), filtered. The crude oil was purified over silica gel (CH2Cl2/MeOH 39:1): colorless oil 0.16 g (49%);

Workup

  1. customthe turbid reaction mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure and ethyl acetate
  3. additionwas added to the residue
  4. washby washing with NaHCO3 (½ sat., 3×), water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe crude oil was purified over silica gel (CH2Cl2/MeOH 39:1)

Sources & evidence

ORD record
ord-e95aa7a14fcd43ca88d05667ebcf7881
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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