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

HRID 460125

반응식

HRID 460125 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8eab4c4ad37c4428a8b9f64aa57973b6
출처 데이터셋
uspto-grants-2007_03
특허 번호
US07196102B2

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