Sodium Bicarbonate → Methyl [4-(4-hydroxyphenyl)-3-methyl-1,2-oxazol-5-yl]acetate

HRID 922244Notes

Reaction equation

HRID 922244 reaction equation
I[C:2]1[C:3]([CH3:12])=[N:4][O:5][C:6]=1[CH2:7][C:8]([O:10][CH3:11])=[O:9].[OH:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])(O)=O.[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CN(C=O)C>[OH:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[C:3]([CH3:12])=[N:4][O:5][C:6]=2[CH2:7][C:8]([O:10][CH3:11])=[O:9])=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 66685715(4-Iodo-3-methylisoxazol-5-yl)acetic acid methyl ester

Product 1

HCID 86695756Methyl [4-(4-hydroxyphenyl)-3-methyl-1,2-oxazol-5-yl]acetateYield 66.6%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

To a 50 mL two neck RB flask fitted with magnetic stirrer was charged with 5 mL of DMF. To the stirred solvent were added methyl (4-iodo-3-methyl-1,2-oxazol-5-yl)acetate (0.7 g, 2.5 mmol), (4-hydroxyphenyl)boronic acid (0.34 g, 2.5 mmol) and 1 mL of aqueous NaHCO3 solution (0.62 g, 7.47 mmol) under argon atmosphere. After purging the argon gas about 10 minutes was added bis-(triphenylphosphine) palladium(II)chloride (0.21 g, 0.3 mmol) and heated at 85° C. for 4 h. The RM was filtered through celite and washed with cold water and extracted with ethyl acetate (25 mL). The organic layer was washed with water (20 mL) and saturated brine solution (20 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by silica gel column chromatography using ethyl acetate and petroleum ether as eluents. The product was obtained as brown solid (0.4 g, yield: 66.6%). 1H NMR (300 MHz, CDCl3): δ 7.07-7.10 (d, 2H), 6.84-6.86 (d, 2H), 5.82 (s, 1H), 3.69 (s, 2H), 3.66 (s, 3H), 2.21 (s, 3H).

Workup

  1. customAfter purging the argon gas about 10 minutes
  2. filtrationThe RM was filtered through celite
  3. washwashed with cold water
  4. extractionextracted with ethyl acetate (25 mL)
  5. washThe organic layer was washed with water (20 mL) and saturated brine solution (20 mL)
  6. dry with materialThe organic layer was dried over anhydrous Na2SO4
  7. customthe solvent was removed under reduced pressure
  8. customThe crude material was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9e3cd2eec78b4e089af2418cd3dcd7d0
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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