Potassium Carbonate → HCID 68465652, compound

HRID 453506Notes

Reaction equation

HRID 453506 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[Cl:22][C:23]1[CH:40]=[CH:39][C:26]([CH2:27][CH2:28][NH:29][C:30](=[O:38])[C:31]2[CH:36]=[CH:35][C:34](F)=[CH:33][CH:32]=2)=[CH:25][CH:24]=1>CS(C)=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH2:27][CH2:28][NH:29][C:30]([C:31]2[CH:32]=[CH:33][C:34]([O:1][C:2]3[CH:3]=[CH:4][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:6][CH:7]=3)=[CH:35][CH:36]=2)=[O:38])=[CH:39][CH:40]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 737426HCID 737426, compoundHCID 15932404Tert-butyl 2-(4-hydroxyphenyl)acetate

Product 1

HCID 68465652HCID 68465652, compoundYield 4.5%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolventHCID 10340Sodium CarbonateSolvent

Conditions

Temperature
85 °C

Procedure

Tert-butyl 2-(4-hydroxyphenyl)acetate (200 mg, 0.960 mmol) was diluted with DMSO (4 mL) followed by the addition of K2CO3 (133 mg, 0.960 mmol) and N-(4-chlorophenethyl)-4-fluorobenzamide (267 mg, 0.960 mmol). The reaction was stirred at 85° C. overnight, and then stirred at 138° C. for 12 hours. The reaction was cooled to ambient temperature, diluted with DCM and 10% aq. sodium carbonate. The layers were separated and the organic layer was dried over MgSO4, filtered and concentrated. The crude material was purified by silica gel chromatography, eluting with hexanes:ethyl acetate (4:1) to yield tert-butyl 2-(4-(4-((4-chlorophenethyl)carbamoyl)phenoxy)phenyl)acetate (20 mg, 4.47% yield) as an off white solid.

Workup

  1. stirringstirred at 138° C. for 12 hours
  2. temperatureThe reaction was cooled to ambient temperature
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material was purified by silica gel chromatography
  8. washeluting with hexanes:ethyl acetate (4:1)

Sources & evidence

ORD record
ord-3c47ee54d85d465bac1a0f4a5ed1f1fd
Source dataset
uspto-grants-2013_07
Patent number
US08492437B2

Reaction notes

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