Ethyl 3-(4-pyridyl)-3-oxopropionate → 1,1'-(2-Hydroxy-5-methyl-1,3-phenylene)di(ethan-1-one)

HRID 253044

반응식

HRID 253044 반응식
O=[C:2](C1C=CN=CC=1)CC(OCC)=O.[OH:15][C:16]1[C:21]([CH2:22][O:23]C)=[CH:20][C:19]([CH3:25])=[CH:18][C:17]=1[C:26](=[O:28])[CH3:27].CC(C)([O-])C.[K+]>C1COCC1.C(OCC)(=O)C.Cl[Pd]Cl>[C:26]([C:17]1[C:16]([OH:15])=[C:21]([C:22](=[O:23])[CH3:2])[CH:20]=[C:19]([CH3:25])[CH:18]=1)(=[O:28])[CH3:27]

참가 물질

7

반응물 3

HCID 2735202Ethyl 3-(4-pyridyl)-3-oxopropionateHCID 132292322'-Hydroxy-5'-methyl-3'-methoxymethylacetophenoneHCID 23665647Potassium tert-butoxide

생성물 1

HCID 23050491,1'-(2-Hydroxy-5-methyl-1,3-phenylene)di(ethan-1-one)

시약·촉매·용매 3

HCID 24290Palladium Chloride촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of a bromo derivative 1 (324 mg, 1 mmol), (R)-(+)-α-methylbenzylamine 2 (122 mg, 1 mmol), potassium t-butoxide (225 mg, 2 mmol) and PdCl2 (dppf) (35 mg, 0.05 mmol) in THF was stirred at refluxing temperature for 20 hours over a nitrogen atmosphere. The reaction mixture was cooled and diluted with ethyl acetate. The organic layer was washed with water, brine and dried over Na2SO4. The ethyl acetate layers was concentrated in vacuo and the residue was subjected to column chromatography (silica gel, ethylacetate) to give the required product 3. 1H NMR (300 MHz, CDCl3), δ 8.78 (br s, 2H), 8.21 (s, 1H), 7.92 (d, J=5.9 Hz, 2H), 7.4-7.26 (m, 5H), 6.90 (s, 1H), 6.50 (d, J=5.5 Hz, 1H, —NH), 6.27 (s, 1H), 4.60 (m, 1H), 2.23 (s, 3H), 1.71 (d, J=6.9 Hz, 3H). MS (m/z)=357.13 (m+1).

후처리

  1. temperatureat refluxing temperature for 20 hours over a nitrogen atmosphere
  2. temperatureThe reaction mixture was cooled
  3. washThe organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. concentrationThe ethyl acetate layers was concentrated in vacuo

출처 및 근거

ORD 기록
ord-d92d745f475c4858b305487e4cd31f5c
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07872011B2

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