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

HRID 252786

反応式

HRID 252786 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 13157012Methyl 5-methyl-1-benzofuran-2-carboxylate収率 42.1%

試薬・触媒・溶媒 2

HCID 74236Tetrabutylammonium Bromide触媒HCID 1140Toluene溶媒

反応条件

温度
25 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-f0578fae2ccf428f9e2a98a5f3ef6004
出典データセット
uspto-grants-2011_01
特許番号
US07868204B2

関連ノート

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