Methyl Acrylate → Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

HRID 1898760노트

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HRID 1898760 반응식
[C:1]([O:4][C:5]1[CH:12]=[C:11](Br)[C:8]([CH:9]=[O:10])=[CH:7][C:6]=1[O:14][CH3:15])(=[O:3])[CH3:2].C(N(CC)CC)C.[C:23]([O:27][CH3:28])(=[O:26])[CH:24]=[CH2:25]>CN(C=O)C.CCOCC.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:4][C:5]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([CH:9]=[O:10])=[C:11]([CH:12]=1)[CH:25]=[CH:24][C:23]([O:27][CH3:28])=[O:26])(=[O:3])[CH3:2]

참가 물질

8

반응물 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 2623485-Bromo-4-formyl-2-methoxyphenyl acetate

생성물 1

HCID 53756943Methyl 5-Acetoxy-2-formyl-4-methoxycinnamate

시약·촉매·용매 4

HCID 178419050HCID 178419050, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
135 °C

실험 절차

To a degassed solution of 4-acetoxy-6-bromo-3-methoxybenzaldehyde (15.4 g), and bis(triphenylphosphine)palladium (11) (1.2 g) in DMF (150 ml) is added triethylamine (31.9 ml) and methyl acrylate (19.6 g). The mixture is heated 135° C. for about 1.5 hours, cooled to room temperature and diluted with ether and water. The organic layer is washed with water, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified by HPLC, eluting with 33% ethyl acetate in hexanes, then methylene chloride, to give the desired product.

후처리

  1. temperaturecooled to room temperature
  2. washThe organic layer is washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by HPLC
  7. washeluting with 33% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-6d60ba4013af443b98f7ff64911150e8
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05571506

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