Potassium Carbonate → Methyl 5-methyl-1-benzofuran-2-carboxylate

HRID 252786

반응식

HRID 252786 반응식
[CH3:1][C:2]1[CH:9]=[C:6]([CH:7]=O)[C:5]([OH:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[CH3:17][O:18][C:19](=[O:26])[CH:20](Br)C(OC)=O>[N+](CCCC)(CCCC)(CCCC)CCCC.[Br-].C1(C)C=CC=CC=1>[CH3:17][O:18][C:19]([C:20]1[O:10][C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:9][C:6]=2[CH:7]=1)=[O:26]

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 69184Benzaldehyde, 2-hydroxy-5-methyl-HCID 70087Dimethyl bromomalonate

생성물 1

HCID 13157012Methyl 5-methyl-1-benzofuran-2-carboxylate수율 42.1%

시약·촉매·용매 2

HCID 74236Tetrabutylammonium Bromide촉매HCID 1140Toluene용매

반응 조건

온도
25 °C

실험 절차

A stirring suspension of 5-methylsalicylaldehyde (1.0 mg, 7.5 mmol), K2CO3 (1.55 g, 11.0 mmol), and Bu4NBr (322 mg, 1 mmol) in toluene (30 ml) was treated with dimethylbromomalo-nate (1.06 ml, 8.0 mmol). The suspension was heated to reflux with a Dean-Stark trap for 20 h. The brown suspension was cooled to 25° C. and concentrated in vacuo. The residue was taken in DCM and filtered. The filtrate was washed with H2O, 1N NaOH and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by column chromatography (10% ethyl acetate/hexane) to afford the title compound 583 (600 mg, 42% yield). LRMS: 190.2 (Calc.); 191.1 (found).

후처리

  1. temperatureThe suspension was heated
  2. temperatureto reflux with a Dean-Stark trap for 20 h
  3. concentrationconcentrated in vacuo
  4. filtrationfiltered
  5. washThe filtrate was washed with H2O, 1N NaOH and brine
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude residue was purified by column chromatography (10% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-f0578fae2ccf428f9e2a98a5f3ef6004
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868204B2

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