Potassium Carbonate → 4-Methoxy-3-(2-methylbenzoxazol-5-yl)benzenecarboxaldehyde

HRID 460125

反応式

HRID 460125 の反応式
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([O:12][CH3:13])=[C:7](B(O)O)[CH:8]=1)=[O:2].[CH3:14][C:15]1[O:16][C:17]2[CH:23]=[CH:22][C:21](Br)=[CH:20][C:18]=2[N:19]=1.C([O-])([O-])=O.[K+].[K+]>C(O)C.C1(C)C=CC=CC=1>[CH3:13][O:12][C:6]1[CH:5]=[CH:4][C:3]([CH:1]=[O:2])=[CH:8][C:7]=1[C:21]1[CH:22]=[CH:23][C:17]2[O:16][C:15]([CH3:14])=[N:19][C:18]=2[CH:20]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 101045995-Bromo-2-methyl-1,3-benzoxazole

生成物 1

HCID 223915884-Methoxy-3-(2-methylbenzoxazol-5-yl)benzenecarboxaldehyde収率 89.6%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 1140Toluene溶媒

実験手順

A solution of 5-formyl-2-methoxybenzeneboronic acid (1 g, 5.6 mmol), 2-methyl-5-bromobenzoxazole (1 g, 4.72 mmol) and K2CO3 (1.63 g, 11.8 mmol) in ethanol (20 mL) and toluene (40 mL) was degassed prior to addition of Pd(Ph3)4 (55 mg, 0.047 mmol). The mixture was refluxed for 20 hours then cooled and filtered through diatomaceous earth. The filtrate was concentrated in vacuo, extracted with ethyl acetate, washed with water and the organic layer dried over sodium sulphate. The crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4) to give 1.13 g of title compound.

後処理

  1. temperatureThe mixture was refluxed for 20 hours
  2. temperaturethen cooled
  3. filtrationfiltered through diatomaceous earth
  4. concentrationThe filtrate was concentrated in vacuo
  5. extractionextracted with ethyl acetate
  6. washwashed with water
  7. dry with materialthe organic layer dried over sodium sulphate
  8. customThe crude was purified by column chromatography (heptane/ethyl acetate 7/3 to 6/4)

出典と根拠

ORDレコード
ord-8eab4c4ad37c4428a8b9f64aa57973b6
出典データセット
uspto-grants-2007_03
特許番号
US07196102B2

関連ノート

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