Sodium Carbonate → HCID 70172846, 화합물

HRID 1936987노트

반응식

HRID 1936987 반응식
[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]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 21837982Methyl 4-(((trifluoromethyl)sulfonyl)oxy)-2,5-dihydrofuran-3-carboxylateHCID 22462508HCID 22462508, 화합물

생성물 1

HCID 70172846HCID 70172846, 화합물수율 87%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-e8dcc4689c8545fc8e6206c17e394ddb
출처 데이터셋
uspto-grants-2002_05
특허 번호
US06391887B1

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