Water → Methyl 5-[(4-ethylphenyl)methyl]-3-hydroxy-2-naphthoate

HRID 221945Notes

Reaction equation

HRID 221945 reaction equation
[OH:1][C:2]1[C:3]([C:20]([O:22][CH3:23])=[O:21])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9](OS(C(F)(F)F)(=O)=O)[CH:8]=[CH:7][CH:6]=2.C(=O)([O-])[O-].[Cs+].[Cs+].O>O1CCCC1.[Pd](Cl)Cl.C1(P([C-]2C=CC=C2)C2C=CC=CC=2)C=CC=CC=1.[CH-]1C=CC=C1.[Fe+2]>[CH2:9]([C:10]1[CH:11]=[CH:2][C:3]([CH2:20][C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[C:10]=2[CH:11]=[C:2]([OH:1])[C:3]([C:20]([O:22][CH3:23])=[O:21])=[CH:4]3)=[CH:4][CH:5]=1)[CH3:8]

Participants

6

Reactant 3

HCID 962Water2×HCID 10796Cesium carbonateHCID 59488801Methyl 3-hydroxy-5-trifluoromethanesulfonyloxy-2-naphthoate

Product 1

HCID 59488750Methyl 5-[(4-ethylphenyl)methyl]-3-hydroxy-2-naphthoateYield 151.4%

Reagents, catalysts & solvents 2

HCID 178479793cyclopenta-1,3-diene;cyclopenta-2,4-dien-1-yl(diphenyl)phosphane;dichloropalladium;iron(2+)CatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

Under a nitrogen stream, the known compound methyl 3-hydroxy-5-trifluoromethanesulfonyloxy-2-naphthoate (Bull. Korean Chem. Soc. 2000, 21, 757; 82.3 mg, 0.23 mmol), diphenylphosphino ferrocene palladium dichloride (17.3 mg, 0.021 mmol), 2-[(4-ethylphenyl)methyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborane (57.8 mg, 0.24 mmol) and cesium carbonate (228.6 mg, 0.70 mmol) were dissolved in tetrahydrofuran (2.0 mL). Water (0.2 mL) was added thereto, and then the mixture was stirred for 30 minutes at 100° C. in a microwave apparatus. Water was added thereto, and the resultant mixture was extracted with ethyl acetate. The organic layer was washed with 1 N hydrochloric acid and saturated brine, dried over anhydrous magnesium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:20)), to thereby obtain the titled compound (55.8 mg, 74%).

Workup

  1. extractionthe resultant mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 1 N hydrochloric acid and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel flash column chromatography (developing solution=ethyl acetate:n-hexane (1:20))

Sources & evidence

ORD record
ord-234646172ba64e6b8bea8366d40eefeb
Source dataset
uspto-grants-2012_06
Patent number
US08207134B2

Reaction notes

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