(4-Methoxyphenyl)boronic acid → HCID 54169979, 화합물

HRID 1377905노트

반응식

HRID 1377905 반응식
[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12](I)=[CH:11][CH:10]=1)[CH3:2].[CH3:17][O:18][C:19]1[CH:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.C([O-])(O)=O.[Na+]>COCCOC.C(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>[CH2:1]([O:3][C:4](=[O:16])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH3:17])=[CH:20][CH:21]=2)=[CH:11][CH:10]=1)[CH3:2]

참가 물질

7

반응물 3

HCID 201262(4-Methoxyphenyl)boronic acidHCID 516892Sodium BicarbonateHCID 53642638HCID 53642638, 화합물

생성물 1

HCID 54169979HCID 54169979, 화합물수율 57.3%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 80711,2-Dimethoxyethane용매

실험 절차

To a solution in ethylene glycol dimethyl ether (30 mL) of 4-(4-iodophenoxy)butyric acid ethyl ester (0.50 g, 1.5 mmol), prepared as in Example 5, step 1, was added tetrakis(triphenylphosphine)palladium(0) (87 mg, 75 μM), and the mixture was stirred for 15 minutes. A solution in ethanol (9.6 mL) of 4-methoxyphenylboronic acid (0.25 g, 1.64 mmol) was then added. Saturated aqueous NaHCO3 (15 mL) was then poured in quickly and the reaction mixture was warmed to reflux and heated for one hour. The reaction mixture was cooled to ambient temperature and concentrated in vacuo. The residue was partitioned between ethyl acetate and 10% aqueous Na2CO3. The organic phase was washed with 10% aqueous Na2CO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. Chromatography on silica gel (20:1, then 10:1, then 5:1 hexane/ethyl acetate) gave 4-[4-(4-methoxyphenyl)phenoxy]butanoic acid ethyl ester (0.27 g, 57%) as white feathery needles.

후처리

  1. temperaturewas warmed
  2. temperatureto reflux
  3. temperatureheated for one hour
  4. concentrationconcentrated in vacuo
  5. customThe residue was partitioned between ethyl acetate and 10% aqueous Na2CO3
  6. washThe organic phase was washed with 10% aqueous Na2CO3 and brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-600e11847d6d45799734fe452ae3a198
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05665777

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