Sodium Carbonate → HCID 70172846, compound

HRID 1936987Notes

Reaction equation

HRID 1936987 reaction equation
[C:1]([NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1OB(O)O)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3].[CH3:18][O:19][C:20]([C:22]1[CH2:26][O:25][CH2:24][C:23]=1OS(C(F)(F)F)(=O)=O)=[O:21].C([O-])([O-])=O.[Na+].[Na+]>COCCOC.C(OCC)(=O)C.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>[CH3:18][O:19][C:20]([C:22]1[CH2:26][O:25][CH2:24][C:23]=1[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[NH:7][C:1](=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3])=[O:21]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 21837982Methyl 2,5-dihydro-4-[[(trifluoromethyl)sulfonyl]oxy]-3-furancarboxylateHCID 22462508HCID 22462508, compound

Product 1

HCID 70172846HCID 70172846, compoundYield 87%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-(Pivaloylamino)phenylboric acid (F. Guiller, F. Nivoliers, A. Godard, F. Marsais, G. Quéguiner, M. A. Siddiqui, V. Snieckus, J. Org. Chem. 1995, 60, 292) (0.66 g, 3.0 mmol), 3-(trifluoromethylsulfonyloxy)-2,5-dihydrofuran-4-carboxylic acid-methyl ester (0.69 g, 2.5 mmol), tetrakis(triphenylphosphine)palladium (69 mg, 0.06 mmol) and a 2M aqueous Na2CO3 solution (1.26 ml, 2.52 mmol) are refluxed in DME (40 ml) for 2.5 hours. The batch is diluted with ethyl acetate, washed with water and saturated NaCl, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with ethyl acetate-hexane yields 0.65 g (87%) of 4-(2-(pivaloylamino)phenyl)-2,5-dihydrofuran-3-carboxylic acid-methyl ester (flash point 105-6° C.). 0.59 g (1.94 mmol) of it is then refluxed in concentrated hydrochloric acid for 2 hours. The batch is poured onto ice and extracted with ethyl acetate and dichloromethane. After drying (Na2SO4) and concentration by evaporation, the residue is heated for two more hours with concentrated HCl and worked up as described: 0.22 g (58%) of product.

Workup

  1. washwashed with water and saturated NaCl
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-e8dcc4689c8545fc8e6206c17e394ddb
Source dataset
uspto-grants-2002_05
Patent number
US06391887B1

Reaction notes

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