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

HRID 1072228

反応式

HRID 1072228 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-aa60f609c0394026adfd3b91ea13627b
出典データセット
uspto-grants-2005_06
特許番号
US06908935B2

関連ノート

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