Potassium Carbonate → HCID 11324480, compound

HRID 987588Notes

Reaction equation

HRID 987588 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1B(O)O.[C:14]([C:17]1[CH:18]=[CH:19][C:20](OS(C(F)(F)F)(=O)=O)=[C:21]([CH:26]=1)[C:22]([O:24][CH3:25])=[O:23])(=[O:16])[CH3:15].C([O-])([O-])=O.[K+].[K+].C([O-])(O)=O.[Na+]>C(O)C.COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:14]([C:17]1[CH:26]=[C:21]([C:22]([O:24][CH3:25])=[O:23])[C:20]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH3:10])=[CH:8][C:3]=2[O:2][CH3:1])=[CH:19][CH:18]=1)(=[O:16])[CH3:15]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 27343412,4-Dimethoxybenzeneboronic acidHCID 11438780methyl 5-acetyl-2-{[(trifluoromethyl)-sulfonyl]oxy}benzoate

Product 1

HCID 11324480HCID 11324480, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

2,4-Dimethoxyphenylboronic acid (24 g, 134 mmol) was dissolved in ethanol (250 mL). The compound from Step A (21 g, 67 mmol) was dissolved in 1,2-dimethoxyethane (375 mL). The two solutions were mixed with tetrakis(triphenylphosphine)palladium (1 g, 0.9 mmol) and K2CO3 (8.9 g, 64 mmol). The resulting suspension was refluxed for 2 h and then poured into saturated NaHCO3 (1 L). The reaction mixture was extracted three times with CH2Cl2 (400 mL) and dried over Na2SO4. The solvent was removed to yield 35.6 g of crude product which was chromatographed on silica gel with hexane/ethyl acetate (2:1) followed by hexane/ethyl acetate (1:1) to yield 18.3 g (87%) of the title compound. 1H-NMR (400 MHz, CDCl3) δH 2.68 (3H, s, COCH3), 3.73 (3H, s, OCH3), 3.76 (3H, s, OCH3), 3.88 (3H, s, CO2CH3), 6.52 (1H, s ArH), 6.62 (1H, d, ArH), 7.23 (1H, d, ArH), 7.45 (1H, d, ArH), 8.13 (1H, d, ArH), 8.42 (1H, s, ArH).

Workup

  1. temperatureThe resulting suspension was refluxed for 2 h
  2. extractionThe reaction mixture was extracted three times with CH2Cl2 (400 mL)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was removed
  5. customto yield 35.6 g of crude product which
  6. customwas chromatographed on silica gel with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-9ce20344140046bea0858dcf0ae529b5
Source dataset
uspto-grants-2003_10
Patent number
US06632835B2

Reaction notes

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