Potassium Carbonate → 2-{2-Hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl ester

HRID 898485Notes

Reaction equation

HRID 898485 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][O:15]S(C1C=CC(C)=CC=1)(=O)=O.[CH2:26]([O:28][C:29](=[O:43])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37](O)=[CH:36][C:35]=1[CH2:41][OH:42])([CH3:32])[CH3:31])[CH3:27].C(=O)([O-])[O-].[K+].[K+]>C(O)C>[CH2:26]([O:28][C:29](=[O:43])[C:30]([O:33][C:34]1[CH:39]=[CH:38][C:37]([O:15][CH2:14][CH2:13][C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][C:2]=2[CH3:1])=[CH:36][C:35]=1[CH2:41][OH:42])([CH3:32])[CH3:31])[CH3:27]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 120517392-(5-Methyl-2-phenyloxazol-4-yl)ethyl 4-methylbenzenesulfonateHCID 235900102-(4-Hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl ester

Product 1

HCID 235900112-{2-Hydroxymethyl-4-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]phenoxy)-2-methylpropionic acid ethyl esterYield 20%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a 25 mL round bottom flask under a nitrogen atmosphere were charged 0.77 g (2.17 mmol) of toluene-4-sulfonic acid 2-(5-methyl-2-phenyloxazol-4-yl)ethyl ester, and 0.5 g (1.97 mmol) of 2-(4-hydroxy-2-hydroxymethylphenoxy)-2-methylpropionic acid ethyl ester dissolved in 10 mL of absolute ethanol. Next, 0.54 g (3.94 mmol) of potassium carbonate (325 mesh) was added and the reaction was heated to 80° C. for 12 h. The volatiles were removed in vacuo and the crude residue was dissolved in 75 mL EtOAc and washed twice with brine, dried over Na2SO4, and removed in vacuo to give a crude oil. This crude residue was purified using radial chromatography with a 2 mm normal phase silica gel plate, eluting with a step gradient of 5:95 EtOAc:Hex to 35:65 EtOAc:Hex to give a colorless oil (0.17 g, 20%). MS (ES) m/e 452 (M+1).

Workup

  1. customThe volatiles were removed in vacuo
  2. dissolutionthe crude residue was dissolved in 75 mL EtOAc
  3. washwashed twice with brine
  4. dry with materialdried over Na2SO4
  5. customremoved in vacuo
  6. customto give a crude oil
  7. customThis crude residue was purified
  8. washeluting with a step gradient of 5:95 EtOAc

Sources & evidence

ORD record
ord-fbd82574777d4615b1093052269969ca
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

Loading…